5-Fluoro-2,3-dihydro-1H-inden-1-amine → 7-chloro-6-[1-(3-chloro-4-fluoro-phenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 911385Notes

Reaction equation

HRID 911385 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[Cl:27][C:28]1[CH:29]=[C:30]([CH:35]([NH2:37])[CH3:36])[CH:31]=[CH:32][C:33]=1[F:34].FC1C=C2C(=CC=1)C(N)CC2>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:37][CH:35]([C:30]1[CH:31]=[CH:32][C:33]([F:34])=[C:28]([Cl:27])[CH:29]=1)[CH3:36]

Participants

4

Reactant 3

HCID 166663285-Fluoro-2,3-dihydro-1H-inden-1-amineHCID 18543184(-)-3-Chloro-4-fluoro-α-methylbenzenemethanamineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 866296267-chloro-6-[1-(3-chloro-4-fluoro-phenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 65%

Procedure

Use a method similar to the General Procedure 5-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (426 mg, 1.0 mmol) with 1-(3-chloro-4-fluoro-phenyl)-ethylamine Isomer 1 (226 mg, 1.3 mmol). Purify by chromatography on silica gel eluting with EtOAc/hexane (1:7) to give 7-chloro-6-[1-(3-chloro-4-fluoro-phenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (293 mg, 65%).

Workup

  1. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:7)

Sources & evidence

ORD record
ord-51e4aa162ea54491993b7828b6cd2f11
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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