O-Methyltyramine → HCID 50924293, compound

HRID 570415Notes

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.[CH3:31][O:32][C:33]1[CH:38]=[CH:37]C(CCN)=[CH:35][CH:34]=1>>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][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:34]=1

Participants

Reactant 2

HCID 4657O-Methyltyramine

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 50924293HCID 50924293, 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-methoxyphenyl)ethylamine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 393 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.24 (1H, s) 8.14 (0H, t) 8.02 (1H, d, J=5.42 Hz) 7.77 (1H, d, J=5.42 Hz) 7.46 (1H, d, J=5.37 Hz) 7.31 (1H, dd, J=3.34, 2.56 Hz) 7.13 (2H, d, J=8.69 Hz) 6.76-6.84 (3H, m) 6.44 (1H, dd, J=3.49, 1.93 Hz) 3.69 (3H, s) 3.37-3.48 (2H, m) 2.75 (2H, t, J=7.37 Hz)

Sources & evidence

ORD record: ord-ce5c7ecc9ff949f7a07a76a1c9a723b2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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