4-Chloroaniline → HCID 50924296, compound

HRID 570422Notes

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.[Cl:31][C:32]1[CH:38]=CC(N)=C[CH:33]=1>>[Cl: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 2

HCID 78124-Chloroaniline

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 50924296HCID 50924296, 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-chloroaniline instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 369 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (1H, br. s.) 10.12 (1H, s) 9.99 (1H, s) 8.04 (1H, d, J=5.47 Hz) 7.91 (1H, d, J=0.10 Hz) 7.71 (2H, d, J=8.93 Hz) 7.52 (1H, d, J=5.37 Hz) 7.37-7.43 (2H, m) 7.33 (1H, dd, J=3.25, 2.61 Hz) 6.85 (1H, d, J=5.42 Hz) 6.46 (1H, dd, J=3.49, 1.88 Hz)

Sources & evidence

ORD record: ord-7839db9bb2a34836a5b1b5d0a6f27817
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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