p-Fluorophenethylamine → HCID 50923994, compound

HRID 570410Notes

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:37]=[CH:36]C(CCN)=[CH:34][CH:33]=1>>[F:31][C:32]1[CH:37]=[CH:36][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:34][CH:33]=1

Participants

Reactant 2

HCID 4653p-Fluorophenethylamine

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 50923994HCID 50923994, 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-(4-fluorophenyl)ethylamine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 381 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.19 (1H, br. s.) 10.45 (1H, s) 8.21 (1H, t, J=5.76 Hz) 8.07 (1H, d, J=6.64 Hz) 7.86 (1H, d, J=5.27 Hz) 7.42 (1H, dd, J=3.12, 1.76 Hz) 7.36 (1H, d, J=5.27 Hz) 7.18 (2H, dd, J=8.79, 5.66 Hz) 7.00 (2H, t, J=8.98 Hz) 6.73 (1H, d, J=6.44 Hz) 6.63 (1H, d, J=3.32 Hz) 3.39-3.47 (2H, m) 2.75 (2H, t, J=7.22 Hz)

Sources & evidence

ORD record: ord-f0829d382a634f6b8529d81cd4bef359
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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