Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate → HCID 59612635, compound

HRID 472625Notes

Reaction equation

Cl[C:2]1[N:25]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=3[O:20][CH2:21][CH:22]([F:24])[F:23])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:26]([O:30][C:31]([N:33]1[CH2:39][CH2:38][C:37]2[CH:40]=[CH:41][C:42]([NH2:44])=[CH:43][C:36]=2[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C:31]([N:33]1[CH2:39][CH2:38][C:37]2[CH:40]=[CH:41][C:42]([NH:44][C:2]3[N:25]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=5[O:20][CH2:21][CH:22]([F:24])[F:23])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:43][C:36]=2[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

Reactant 2

HCID 11402789Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate

HCID 86648366HCID 86648366, compound

Product 1

HCID 59612635HCID 59612635, compound

Procedure

7-{8-[2-(2,2-Difluoro-ethoxy)-4-methanesulfonyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-[2-(2,2-difluoro-ethoxy)-4-methanesulfonyl-phenyl]-[1,2,4]-triazolo[1,5-a]pyridine (0.371 g, 1.20 mmol) and 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (0.253 g, 652 mmol) in a manner analogous to Example 311a and 311b to give product (0.285 g, 71%): 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.58 (s, 1H), 8.82 (d, 1H), 7.94 (d, 1H), 7.74 (s, 1H), 7.68 (m, 2H), 7.48 (d, 1H), 7.37 (s, 1H), 7.05 (m, 2H), 6.27 (br m, 1H), 4.52 (m, 2H), 3.45 (m, 4H), 2.77 (m, 4H), 2.50 (s, 3H), 1.41 (s, 9H). MS=614 (MH)+.

Sources & evidence

ORD record: ord-37d1eabef70b4204b28a8d51d18d5349
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

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