7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86629612, compound

HRID 911364Notes

Reaction equation

HRID 911364 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.[F:27][C:28]([F:41])([F:40])[CH:29]([CH3:39])[O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>C1(C)C=CC=CC=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:36][CH2:35][C:34]1[CH:37]=[CH:38][C:31]([O:30][CH:29]([CH3:39])[C:28]([F:27])([F:40])[F:41])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 57656088HCID 57656088, compound

Product 1

HCID 86629612HCID 86629612, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (500 mg, 1.2 mmol) with (±)-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzylamine (515 mg, 2.3 mmol) in toluene (10 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1 and 3:1) followed by SCX chromatography [pre-wash column with methanol followed by DCM, load material dissolved in DCM, then elute with DCM/2M ammonia in methanol (1:1) and concentrate in vacuo] to give (±)-7-chloro-6-[4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (530 mg, 90%). GC-MS m/z: 494 (M+).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1 and 3:1)
  2. washpre-wash column with methanol
  3. dissolutiondissolved in DCM
  4. washelute with DCM/2M ammonia in methanol (1:1)
  5. concentrationconcentrate in vacuo]

Sources & evidence

ORD record
ord-988a0040e5c34d488661038730bd1525
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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