4-cyano-1H-pyrrole-2-carboxylic acid → c-FMS inhibitor

HRID 646916

반응식

HRID 646916 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:8]([OH:10])=O)[NH:6][CH:7]=1)#[N:2].[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([N:27]3[CH2:32][CH2:31][CH:30]([CH3:33])[CH2:29][CH2:28]3)[CH:19]=2)[CH2:14][CH2:13]1>>[CH3:11][N:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:8]([C:5]3[NH:6][CH:7]=[C:3]([C:1]#[N:2])[CH:4]=3)=[O:10])=[C:20]([N:27]3[CH2:32][CH2:31][CH:30]([CH3:33])[CH2:29][CH2:28]3)[CH:19]=2)[CH2:16][CH2:17]1

참가 물질

3

반응물 2

HCID 118048114-cyano-1H-pyrrole-2-carboxylic acidHCID 586385301-Methyl-4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-piperazine

생성물 1

HCID 11654378c-FMS inhibitor수율 55.1%

실험 절차

The procedure of Example 53 was followed using 4-cyano-1H-pyrrole-2-carboxylic acid (as prepared in Example 2, 56 mg, 0.22 mmol) and 4-(4-methyl-piperazin-1-yl)-2-(4-methyl-piperidin-1-yl)-phenylamine (as prepared in Example 13, step (a), 61 mg 0.21 mmol). Purification of the resulting residue by silica gel preparative TLC eluting with 10% methanol in dichloromethane yielded 47 mg (55%) of the title compound as an off-white solid. 1H-NMR (400 MHz, CDCl3): δ 9.60 (br s, 1H), 8.30 (d, 1H, J=8.9), 7.24 (d, 1H, J=3.7 Hz), 7.21 (d, 1H, J=3.7 Hz), 6.79 (d, 1H, J=2.7 Hz), 6.73 (dd, 1H, J=8.9, 2.7 Hz), 3.20 (m, 4H), 3.00-2.97 (m, 2H), 2.76-2.70 (m, 2H), 2.59 (m, 4H), 2.37 (s, 3H), 1.85-1.82 (m, 2H), 1.56-1.46 (m, 2H), 1.07 (d, 3H, J=6.2 Hz). LC-MS (ESI, m/z): Calcd. for C23H31N6O, 407.3 (M+H); found: 407.2.

후처리

  1. customPurification of the resulting residue by silica gel preparative TLC
  2. washeluting with 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-295280bcdc004564bc128df82a64cb9d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

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