Methanol → 2-(3-Chlorophenyl)-N-(3-{3-[2-(phenylamino)-4-pyrimidinyl]pyrazolo-[1,5-a]pyridin-2-yl}phenyl)acetamide

HRID 1157543노트

반응식

HRID 1157543 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:42][C:43]1[CH:44]=[C:45]([CH2:49][C:50](O)=[O:51])[CH:46]=[CH:47][CH:48]=1.CO>C1COCC1>[Cl:42][C:43]1[CH:44]=[C:45]([CH2:49][C:50]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[C:16]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[N:18]=4)=[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][N:10]4[N:9]=3)[CH:3]=2)=[O:51])[CH:46]=[CH:47][CH:48]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 158793-Chlorophenylacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 577372234-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

생성물 1

HCID 686855202-(3-Chlorophenyl)-N-(3-{3-[2-(phenylamino)-4-pyrimidinyl]pyrazolo-[1,5-a]pyridin-2-yl}phenyl)acetamide수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidine (30 mg, 0.08 mmol) (see Example 3, Step H) in THF (3 mL) was added CDI (14 mg, 0.09 mmol). The resultant mixture was stirred at rt for 1 hour. To the mixture was added (3-chlorophenyl)acetic acid (15 mg, 0.09 mmol) and then stirred at rt for 15 h. Methanol (2 mL) was added and the mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel (hexanes/EtOAc) to give the title compound (25 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 3.68 (s, 2H), 6.53 (d, 1H, J=5.3 Hz), 6.92 (m, 1H), 6.92 (m, 1H), 7.12 (m, 1H), 7.21-7.50 (m, 9H), 7.68-7.76 (m, 3H), 7.89 (m, 1H), 8.26 (d, 1H, J=5.3 Hz), 8.47 (m, 1H), 8.83 (d, 1H, J=6.8 Hz), 9.56 (s, 1H), 10.35 (s, 1H). ES-LC/MS m/z=531 [M+H]+.

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel (hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-c4b960203377437eadce973393ce6d4a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807673B2

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