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

HRID 570394

反応式

HRID 570394 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-b8940524819d4cb2b9549764911ed045
出典データセット
uspto-grants-2015_05
特許番号
US09023847B2

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