P-Anisidine → HCID 50924297, compound

HRID 570423Notes

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.[CH3:31][O:32][C:33]1[CH:39]=CC(N)=C[CH:34]=1>>[CH3:31][O:32][C:33]1[CH:39]=[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:34]=1

Participants

Reactant 2

HCID 7732P-Anisidine

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 50924297HCID 50924297, 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-methoxyaniline instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 365 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 10.14 (1H, s) 9.73 (1H, s) 8.00 (1H, d, J=5.42 Hz) 7.85 (1H, d, J=5.42 Hz) 7.44-7.55 (3H, m) 7.29 (1H, dd, J=3.20, 2.71 Hz) 6.89 (2H, d, J=8.98 Hz) 6.80 (1H, d, J=5.47 Hz) 6.42 (1H, dd, J=3.47, 1.90 Hz) 3.72 (3H, s)

Sources & evidence

ORD record: ord-21532f5a6bc74e2cbda163db5d19644a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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