4-Fluoroaniline → HCID 50924298, compound

HRID 570424Notes

Reaction equation

C(OC(N1C[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.[F:31][C:32]1[CH:38]=CC(N)=C[CH:33]=1.C(N1CCC(N)C1)(OC(C)(C)C)=O>>[F:31][C:32]1[CH:38]=[CH:9][C: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])=[CH:11][CH:33]=1

Participants

Reactant 3

HCID 97314-Fluoroaniline

HCID 27563701-Boc-3-aminopyrrolidine

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 50924298HCID 50924298, compound

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 4-fluoroaniline of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 353 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (1H, br. s.) 10.11 (1H, s) 9.90 (1H, s) 8.01 (1H, d, J=5.42 Hz) 7.88 (1H, d, J=5.42 Hz) 7.64 (2H, dd, J=9.13, 5.08 Hz) 7.49 (1H, d, J=5.42 Hz) 7.30 (1H, dd, J=3.25, 2.66 Hz) 7.16 (2H, t, J=8.93 Hz) 6.82 (1H, d, J=5.47 Hz) 6.43 (1H, dd, J=3.49, 1.93 Hz)

Sources & evidence

ORD record: ord-1ef0c3fb207647359ccd787f2bbea3b5
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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