3,3,3-Trifluoropropionic acid → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid pyrrolidin-3-ylamide

HRID 570394

반응식

HRID 570394 반응식
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])[CH2:9]1)=O)(C)(C)C.FC(CC(O)=O)(F)F>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])[CH2:9]1

참가 물질

4

반응물 2

HCID 27779723,3,3-Trifluoropropionic acidHCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 509239963-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid pyrrolidin-3-ylamide수율 122.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (50 mg, 0.12 mmol) in methylene chloride (1.0 mL) was added trifluoromethyl acetic acid (1.0 mL). After 1H the solution was concentrated in vacuo, triturated with diethylether to afford 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid pyrrolidin-3-ylamide (48 mg, 99%). LCMS (ESI) 328 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (1H, br. s.) 10.25 (1H, s) 8.08 (1H, d, J=6.83 Hz) 8.02 (1H, d, J=5.47 Hz) 7.81 (1H, d, J=5.27 Hz) 7.48 (1H, d, J=5.47 Hz) 7.32 (1H, d, J=3.51 Hz) 6.81 (1H, d, J=5.47 Hz) 6.44 (1H, d, J=3.51 Hz) 4.32-4.51 (1H, m) 3.14 (1H, dd, J=11.62, 6.74 Hz) 3.02-3.11 (1H, m) 2.89-2.98 (1H, m) 2.86 (1H, dd, J=11.71, 5.08 Hz) 1.97-2.15 (1H, m) 1.68-1.84 (1H, m)

후처리

  1. concentrationAfter 1H the solution was concentrated in vacuo
  2. customtriturated with diethylether

출처 및 근거

ORD 기록
ord-b8940524819d4cb2b9549764911ed045
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023847B2

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