2-Methylphenethylamine → HCID 50924142, compound

HRID 570412Notes

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.C[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1CCN>>[C:34]1([CH3:35])[CH:33]=[CH:32][CH:37]=[CH:36][C:12]=1[CH2:11][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 20638682-Methylphenethylamine

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 50924142HCID 50924142, 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-(2-methylphenyl)ethylamine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 377 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.97 (1H, br. s.) 10.45 (1H, s) 8.28 (1H, t, J=5.66 Hz) 8.06 (1H, d, J=6.25 Hz) 7.84 (1H, d, J=5.47 Hz) 7.36-7.43 (2H, m) 7.01-7.15 (4H, m) 6.78 (1H, d, J=6.25 Hz) 6.59 (1H, d, J=3.51 Hz) 3.39 (2H, td, J=7.52, 6.05 Hz) 2.77 (2H, d, J=7.81 Hz) 2.29 (3H, s)

Sources & evidence

ORD record: ord-f99eb9f868a7465581763669dddfebc5
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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