3-azido-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one → 6-fluoro-3-{4-[2-fluoro-4-(pyridin-4-yl)-phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 2035704Notes

Reaction equation

HRID 2035704 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[F:15])#[CH:2].[N:16]([CH:19]1[CH2:25][CH2:24][C:23]2[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:22]=2[N:21]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:20]1=[O:36])=[N+:17]=[N-:18]>>[F:30][C:26]1[C:23]2[CH2:24][CH2:25][CH:19]([N:16]3[CH:2]=[C:1]([C:3]4[CH:8]=[CH:7][C:6]([C:9]5[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=5)=[CH:5][C:4]=4[F:15])[N:18]=[N:17]3)[C:20](=[O:36])[N:21]([CH2:31][C:32]([F:33])([F:34])[F:35])[C:22]=2[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 580635233-azido-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 580636224-(4-Ethynyl-3-fluorophenyl)pyridine

Product 1

HCID 580636086-fluoro-3-{4-[2-fluoro-4-(pyridin-4-yl)-phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneYield 43.6%

Procedure

Following GP 3, the title compound (32 mg) was prepared using 4-(4-ethynyl-3-fluorophenyl)pyridine (29 mg) and 3-azido-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (58 mg).

Sources & evidence

ORD record
ord-3ef1865f3fb94421840401b6022be9ec
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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