3-Aminobenzamide → 4-(3-Carbamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide

HRID 1391484

반응식

HRID 1391484 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]3)[CH:11]=2)=[CH:4][C:3]=1[NH:27][C:28]([N:30]1[C:34]2[N:35]=[CH:36][N:37]=[C:38](Cl)[C:33]=2[CH:32]=[CH:31]1)=[O:29].[NH2:40][C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44]([NH2:46])=[O:45]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]3)[CH:11]=2)=[CH:4][C:3]=1[NH:27][C:28]([N:30]1[C:34]2[N:35]=[CH:36][N:37]=[C:38]([NH:40][C:41]3[CH:49]=[CH:48][CH:47]=[C:43]([C:44](=[O:45])[NH2:46])[CH:42]=3)[C:33]=2[CH:32]=[CH:31]1)=[O:29]

참가 물질

4

반응물 2

HCID 16453-AminobenzamideHCID 596739784-Chloro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide

생성물 1

HCID 114224004-(3-Carbamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide수율 73%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

4-Chloro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide, (50 mg, 0.09 mmol), prepared as in reference 3, in glacial acetic acid (2 mL) is mixed with 3-aminobenzamide (24.5 mg, 0.18 mmol) and shaken at 80° C. for 24 hours. The resulting mixture is directly purified by preparative HPLC-MS to give 4-(3-carbamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide (42.9 mg, yield 73%); 1H NMR (400 MHz, DMSO-d6) δ 11.54 (s, 1H), 10.65 (s, 1H), 9.96 (s, 1H), 9.68 (s, 1H), 8.59 (d, J=13.1 Hz, 1H), 8.51 (s, 1H), 8.50 (s, 1H), 8.45 (s, 1H), 8.41 (s, 1H), 8.19 (d, J=10.1 Hz, 2H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (s, 1H), 7.83 (d, J=3.9 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.57 (d, J=4.7 Hz, 1H), 7.43 (t, J=7.9 Hz, 1H), 7.35 (s, 1H), 7.30 (d, J=8.5 Hz, 1H), 7.08 (d, J=3.9 Hz, 1H), 2.43 (s, 3H), 2.34 (s, 3H); ESIMS m/z 654.1 (M++1).

후처리

  1. customThe resulting mixture is directly purified by preparative HPLC-MS

출처 및 근거

ORD 기록
ord-af2b8aefbb414e2ca08dcc885fb59ee9
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07338957B2

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