7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624166, compound

HRID 1191121Notes

Reaction equation

HRID 1191121 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:34]=[CH:33][C:32]([O:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:31][N:30]=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:34]=[CH:33][C:32]([O:35][CH:36]2[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]2)=[CH:31][N:30]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495545HCID 58495545, compound

Product 1

HCID 86624166HCID 86624166, compoundYield 65%

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 (705 mg, 1.66 mmol) and 2-aminomethyl-5-cyclohexyloxy-pyridine (410 mg, 1.99 mmol). Purify the crude mixture by chromatography on silica gel (150 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 9:1 gradient) to obtain 7-chloro-6-[(5-cyclohexyloxy-pyridin-2-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (520 mg, 65%). MS (APCI+) m/z: 482 (M+H)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel (150 g, pre-packed cartridge)
  2. washeluting with hexane/EtOAc (1:0 to 9:1 gradient)

Sources & evidence

ORD record
ord-4d2506406d0e48039c0f892620813f5d
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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