Corrigendum to “Synthetic studies on novel Syk inhibitors. Part 1: Synthesis and structure–activity relationships of pyrimidine-5-carboxamide derivatives” [Bioorg. Med. Chem. 13 (2005) 4936–4951]

Bioorganic & Medicinal Chemistry 13 (2005) 6277–6279

Corrigendum

Corrigendum to ‘‘Synthetic studies on novel Syk inhibitors. Part 1: Synthesis and structure–activity relationships of pyrimidine-5-carboxamide derivatives’’ [Bioorg. Med. Chem. 13 (2005) 4936–4951] Hiroyuki Hisamichi,a,* Ryo Naito,a Akira Toyoshima,b Noriyuki Kawano,a Atsushi Ichikawa,a Akiko Orita,a Masaya Orita,a Noritaka Hamada,a Makoto Takeuchi,a Mitsuaki Ohtaa and Shin-ichi Tsukamotoa a

Institute for Drug Discovery Research, Astellas Pharma Inc., 21 Miyukigaoka, Tsukuba, Ibaraki 305-8585, Japan b Department of Clinical Development, Astellas Pharma Inc., 3-17-1 Hasune, Itabashi, Tokyo 174-8612, Japan

The legends to Schemes 1, 2, and 3 do not correspond to their respective schemes. The correct schemes and legends appear on the following two pages.

DOI of original article: 10.1016/j.bmc.2005.05.033. * Corresponding author. Tel.: +81 0 29 863 6741; fax: +81 0 29 852 2971; e-mail: [email protected] 0968-0896/$ - see front matter Ó 2005 Elsevier Ltd. All rights reserved. doi:10.1016/j.bmc.2005.08.007

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Corrigendum / Bioorg. Med. Chem. 13 (2005) 6277–6279

Cl CO2Et a

N 1

R

b

NH 1

1

R

1

N

4 No. 4a 4b 4c

No. 3a H 3b Me 3c Ph

No. 2a H 2b Me 2c Ph

No. 1a H 1b Me 1c Ph

1

R

N

R1

R1

CONH2

N

3

2 R1

NH

CO2H

N

N

R

c

NH

CO2Et

N

N

CF3

CF3

CF3

R1 H Me Ph

Scheme 1. Reagents and conditions: (a) 3-trifluoromethylaniline, iPr2NEt, MeCN; (b) 1 M NaOH, MeOH; (c) aq NH3, EDCI, HOBt, ClCH2CH2Cl.

X Cl

Cl

NH CO2Et

N

X

a

N Cl

N

NH CO2Et

b

N

Cl

NH

NH CONH2

N

No. X 8a 3-CF3 8b H 8c 2-Me 8d 3-Me 8e 4-Me 8f 3-NC 8g 3-Et 8h 3-iPr 8i 3-MeO 8j 3-EtO 8k 3-iPrO 8l 3-Br

N

X

X

O

c

No. X 7a 3-CF3 7b H 7c 2-Me 7d 3-Me 7e 4-Me 7f 3-NC 7g 3-Et 7h 3-iPr 7i 3-MeO 7j 3-EtO 7k 3-iPrO 7l 3-Br

No. X 6a 3-CF3 6b H 6c 2-Me 6d 3-Me 6e 4-Me 6f 3-NC 6g 3-Et 6h 3-iPr 6i 3-MeO 6j 3-EtO 6k 3-iPrO 6l 3-Br

N N N

CO2H

N

d

N

CONH2

2

N

R N N 3 R

No. 9a 9b 9c 9d 9e 9f 9g 9h 9i

R2R3N H2N(CH2)2HN H2N(CH2)4HN BocMeN(CH2)2HN MeHN(CH2)2HN Me2 N(CH 2)2HN Me2N(CH2)2MeN piperazin-1-yl H2N(CH2)2HN H H2N(CH2)2HN 2-Me

X 3-CF3 3-CF3 3-CF3 3-CF3 3-CF3 3-CF3 3-CF3

e

R2R3N X No. 9j 3-Me H2N(CH2)2HN 9k 4-Me H2N(CH2)2HN 9l 3-NC H2N(CH2)2HN 9m 3-Et H2N(CH2)2HN 9n 3-iPr H2N(CH2)2HN 9o 3-MeO H N(CH ) HN 2 2 2 9p 3-EtO H2N(CH2)2HN 9q 3-iPrO H2N(CH2)2HN 9r 3-Br H2N(CH2)2HN

Scheme 2. Reagents and conditions: (a) ArNH2, iPr2NEt, MeCN; (b) 1 M NaOH, MeOH or THF; (c) aq NH3, EDCI, HOBt, ClCH2CH2Cl or DMF; (d) R2R3NH, MeCN; (e) 4 N HCl/AcOEt, EtOH.

Corrigendum / Bioorg. Med. Chem. 13 (2005) 6277–6279 4

R

Cl CO2Et

N S

a

4

R

NH b

CO2Et

N S

N

4

No. 13a 13b 13c 13d 13e

CO2H

S

c

N

No. R4 12a 3-CF3Ph 12b Me 12c cyclohexyl

4

R

NH O

N S

NH

N

N

No. R4 11a 3-CF3Ph 11b Me 11c cyclohexyl R

6279

N

5

R N 6 R

R4 3-CF3Ph Me cyclohexyl 3-CF3Ph 3-CF3Ph

R5 H H H H Me

d 2

R

R6 H H H Me Me

No. 14a 14b 14c 14d 14e 14f

NH O

N N H

N

R2H2N(CH2)3HO(CH2)2H2N(CH2)2H2N(CH2)2H2N(CH2)2H2N(CH2)2-

5

R N 6 R

R4 3-CF3Ph 3-CF3Ph Me cyclohexyl 3-CF3Ph 3-CF3Ph

R5 H H

R6 H H

H H H H H Me Me Me

Scheme 3. Reagents and conditiont: (a) R4NH2, iPr2NEt, MeCN; (b) 1 M NaOH, MeOH; (c) R5R6NH, EDCI, HOBt, ClCH2CH2Cl or DMF; (d) R2NH2, MeCN.