7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624184, compound

HRID 1191149Notes

Reaction equation

HRID 1191149 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([CH2:30][NH:31][C:32]2[S:36][N:35]=[C:34]([C:37]3[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=3)[CH:33]=2)[CH2:29][CH2:28]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:13])[F:14])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:42][CH2:41][C:40]1[CH:39]=[CH:38][C:37]([C:34]2[CH:33]=[C:32]([NH:31][CH2:30][CH:27]3[CH2:29][CH2:28]3)[S:36][N:35]=2)=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 59828902HCID 59828902, compound

Product 1

HCID 86624184HCID 86624184, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (75 mg, 0.18 mmol) with 4-[5-(cyclopropylmethyl-amino)-isothiazol-3-yl]-benzylamine (68 mg, 0.26 mmol) in toluene (3 mL). Purify the crude mixture by chromatography on silica gel (4 g) eluting with hexane/EtOAc with 2% methanol (9:1 to 4:1 gradient) to obtain 7-chloro-6-{4-[5-(cyclopropylmethyl-amino)-isothiazol-3-yl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (38 mg, 40%). MS (ES+) m/z: 535.3 (M+H)4.

Workup

  1. customPurify the crude mixture by chromatography on silica gel (4 g)
  2. washeluting with hexane/EtOAc with 2% methanol (9:1 to 4:1 gradient)

Sources & evidence

ORD record
ord-6ae727bf593d4bc78c2bedc5f79007c1
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…