Pyrrolidine → Pyrrolidin-1-yl-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone

HRID 570392

Reaction equation

C(OC(N1CCC(N[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])C1)=O)(C)(C)C.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[N:31]1([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])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Reactant 2

HCID 31268Pyrrolidine

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

Product 1

HCID 66957443Pyrrolidin-1-yl-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone

Procedure

This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using pyrrolidine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 313 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.40 (1H, br. s.) 10.62 (1H, s) 8.07 (1H, d, J=6.83 Hz) 7.88 (1H, d, J=5.27 Hz) 7.39 (1H, d, J=3.51 Hz) 7.29 (1H, d, J=5.47 Hz) 6.72 (1H, d, J=3.32 Hz) 6.70 (1H, d, J=6.64 Hz) 3.42 (1H, br. s.) 2.47 (4H, dt, J=3.66, 1.78 Hz) 1.75 (4H, br. s.)

Sources & evidence

ORD record: ord-9297d821120e4f5da4df3677cf279d89
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Linked notes

Loading…