2-(3-Fluorophenyl)ethanamine → HCID 50924140, compound

HRID 570409Notes

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.[F:31][C:32]1[CH:33]=C(CCN)[CH:35]=[CH:36][CH:37]=1>>[F:31][C:32]1[CH:33]=[C:12]([CH2:11][CH2:10][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:35]=[CH:36][CH:37]=1

Participants

Reactant 2

HCID 5339282-(3-Fluorophenyl)ethanamine

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 50924140HCID 50924140, 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 2-(3-fluorophenyl)ethylamine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 381 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.87 (1H, br. s.) 10.38 (1H, s) 8.22 (1H, t, J=5.66 Hz) 8.05 (1H, d, J=6.05 Hz) 7.82 (1H, d, J=5.47 Hz) 7.42 (1H, d, J=5.27 Hz) 7.37 (1H, d, J=3.51 Hz) 7.26 (1H, td, J=8.00, 6.44 Hz) 7.04 (2H, dd, J=8.00, 2.54 Hz) 6.98 (1H, td, J=8.88, 2.93 Hz) 6.77 (1H, d, J=6.05 Hz) 6.54 (1H, d, J=3.51 Hz) 3.42-3.51 (2H, m) 2.82 (2H, t, J=7.13 Hz)

Sources & evidence

ORD record: ord-f8191c7f1c0641fda4096d868fd7c56a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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