7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86629687, compound

HRID 911693Notes

Reaction equation

HRID 911693 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.[CH:27]1([S:33][C:34]2[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCOCC1>[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:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([S:33][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 57656337HCID 57656337, compound

Product 1

HCID 86629687HCID 86629687, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Use a method similar to the General Procedure 5-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (167 mg, 0.392 mmol) with 4-cyclohexylthio-benzylamine (95.4 mg, 0.431 mmol) in anhydrous 1,4-dioxane (5 mL). Purify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 13:7 gradient) to obtain 7-chloro-6-(4-cyclohexylthio-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (155 mg, 79%). MS (ES+) m/z: 519 (M+Na)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 13:7 gradient)

Sources & evidence

ORD record
ord-3d28e96c8d9c40819308e85b150f7253
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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