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

HRID 570394

Reaction equation

HRID 570394 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)

Workup

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

Sources & evidence

ORD record
ord-b8940524819d4cb2b9549764911ed045
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Linked notes

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