4'-(Bromomethyl)-2-cyanobiphenyl → 3(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-cyano[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-2-one

HRID 1740258Notes

Reaction equation

HRID 1740258 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:17]([O:21][C:22]([NH:24][C@@H:25]1[CH2:31][CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[NH:27][C:26]1=[O:36])=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22]([NH:24][C@@H:25]1[CH2:31][CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[N:27]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]#[N:16])=[CH:5][CH:4]=2)[C:26]1=[O:36])=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 10923829(R)-(2-Oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 228774623(R)-t-Butoxycarbonylamino-2,3,4,5-tetrahydro-1-[[2'-cyano[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-2-one

Procedure

Prepared from 4'-bromomethyl-1,1'-biphenyl-2-nitrile (prepared by the method of M. Fisher, et al, U.S. Pat. No. 5,206,235) and 3(R)-t-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Step A) by the procedure described in Example 1, Step Q. 1H NMR (400 MHz, CDCl3): δ 1.39 (s, 9H), 1.90 (m, 1H), 2.40-2.60 (m, 3H), 4.28 (m, 1H), 4.94 (d, 15 Hz, 1H), 5.20 (d, 15 Hz, 1H), 5.43 (d, 7 Hz, 1H), 7.1-7.3 (m, 4H), 7.33 (d, 8 Hz, 2H), 7.35-7.50 (m, 4H), 7.60 (t, 8 Hz, 1H), 7.72 (d, 8 Hz, 1H). FAB-MS: calculated for C29H29N3O3 467; found 468 (M+H, 15%), 368 (M-BOC, 100%).

Workup

  1. customprepared by the method of M

Sources & evidence

ORD record
ord-0f11cbfa0bb74306a76af6ef499a72f0
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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