Benzenemethanamine, 3-chloro- → HCID 50924294, compound

HRID 570417Notes

Reaction equation

C(OC(N1[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])C1)=O)(C)(C)C.[Cl:31][C:32]1[CH:33]=C(C=[CH:38][CH:39]=1)CN>>[Cl:31][C:32]1[CH:33]=[C:11]([CH:12]=[CH:38][CH:39]=1)[CH2:10][NH:13][C:14]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][CH:29]=[CH:30][C:23]=12)=[O:15]

Participants

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-

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 50924294HCID 50924294, 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 3-chlorobenzylamine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 383 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (1H, br. s.) 10.27 (1H, s) 8.72 (1H, t, J=5.95 Hz) 8.03 (1H, d, J=5.47 Hz) 7.82 (1H, d, J=5.47 Hz) 7.50 (1H, d, J=5.47 Hz) 7.21-7.41 (5H, m) 6.84 (1H, d, J=5.47 Hz) 6.41 (1H, dd, J=3.51, 1.95 Hz) 4.46 (2H, d, J=5.86 Hz)

Sources & evidence

ORD record: ord-e6ab0902859c4064830cfee0ee79b88e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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