7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624182, compound

HRID 1191148Notes

Reaction equation

HRID 1191148 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.[NH2:27][CH2:28][C:29]1[CH:30]=[N:31][C:32]([O:35][CH2:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:33][CH:34]=1>>[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:27][CH2:28][C:29]1[CH:30]=[N:31][C:32]([O:35][CH2:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495447HCID 58495447, compound

Product 1

HCID 86624182HCID 86624182, compoundYield 50%

Procedure

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (210 mg, 0.5 mmol) with 3-aminomethyl-6-(3,3-dimethyl-2-oxo-butoxy)-pyridine (220 mg, 1 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to give 7-chloro-6-{[6-(3,3-dimethyl-2-oxo-butoxy)-pyridin-3-ylmethyl]-amino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (122 mg, 50%). MS (ES+) m/z: 498 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-77bc00e2c15547adaf77534f058929d5
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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