Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate → 7-[8-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester

HRID 1890009Notes

Reaction equation

HRID 1890009 reaction equation
Cl[C:2]1[N:19]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][O:17][CH3:18])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:33][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([NH2:38])=[CH:37][C:30]=2[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([O:24][C:25]([N:27]1[CH2:33][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([NH:38][C:2]3[N:19]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=5[CH2:16][O:17][CH3:18])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:37][C:30]=2[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 11402789Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylateHCID 674814042-chloro-8-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 498382737-[8-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester

Procedure

2-Chloro-8-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-2-chloro[1,2,4]triazolo[1,5-a]pyridine (0.71 g, 3.0 mmol) and 2-methoxymethyl)phenylboronic acid (0.71 g, 4.3 mmol) in a manner analogous to Example 2c. Product was isolated as a foam (0.82 g, 98%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.55 (d, J=6.3 Hz, 1H), 7.64-7.57 (m, 2H), 7.50-7.43 (m, 1H), 7.25-7.21 (m, 2H), 7.17 (t, J=7.3 Hz, 1H), 4.37 (s, 2H), 3.27 (s, 3H), MS=328 (MH)+. 241b) 7-[8-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (0.40 g, 1.46 mmol) and 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (0.46 g, 1.75 mmol) in a manner analogous to Example 2d. Product was isolated as a foam (0.5 g, 70%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.48 (d, J=6 Hz, 1H), 7.61 (d, J=6 Hz, 1H), 7.51-7.42 (m, 4H), 7.00-6.89 (m, 3H), 6.79 (s, 1H), 3.62-3.45 (m, 4H), 3.29 (s, 3H), 2.84-2.74 (m, 4H), 1.52 (s, 9H). MS=500 (MH)+.

Sources & evidence

ORD record
ord-338ca8868e384912a404f7902efe52a8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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