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

HRID 1191117Notes

Reaction equation

HRID 1191117 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.NCC1C=NC(CSCC(C)(C)C)=CC=1>O1CCOCC1>[CH2:10]1[C:4]2[CH:3]=[CH:2][CH:18]=[CH:17][C:5]=2[CH2:6][CH2:7][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495614HCID 58495614, compound

Product 1

HCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepineYield 99.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Use a method similar to the General Procedure 1-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (586 mg, 1.37 mmol) with 3-aminomethyl-6-[(2,2-dimethylpropyl)thiomethyl]-pyridine (340 mg, 1.51 mmol) in 1,4-dioxane (15 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1 and 3:1) followed by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1). Concentrate in vacuo to obtain 7-chloro-6-{6-[(2,2-dimethyl-propylthiomethyl)-pyridin-3-ylmethyl]-amino}trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (0.2 g, 29%).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1 and 3:1)
  2. washeluting with DCM and DCM/2M ammonia in methanol (1:1)
  3. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-6d98c7a96f7744b78218fe6ce2c4d285
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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