Chlorosulfamic acid → 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-sulfonamide
Reaction equation
[CH2:1]([C:9]1[C:10]([C:22]([F:25])([F:24])[F:23])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CCN)CC)C.[S:34](Cl)(=[O:37])(=[O:36])[NH2:35]>ClCCl>[CH2:1]([C:9]1[C:10]([C:22]([F:25])([F:24])[F:23])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH:20]([S:34]([NH2:35])(=[O:37])=[O:36])[CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (93 mg, 0.24 mmol) in dichloromethane (3 mL) was added diethylaminoethyl amine (0.13 mL, 0.73 mmol) and sulfamoyl chloride (42 mg, 0.37 mmol). After stirring overnight, another portion of sulfamoyl chloride (42 mg) was added at 0° C., and the resulting mixture stirred for 2 h at room temperature. The resulting mixture was then concentrated under reduced pressure, and the residue was purified by reverse-phase chromatography (gradient 42%→90% TFA-H2O:acetonitrile) to yield 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-sulfonamide (32 mg).
Workup
- stirringthe resulting mixture stirred for 2 h at room temperature
- concentrationThe resulting mixture was then concentrated under reduced pressure
- customthe residue was purified by reverse-phase chromatography (gradient 42%→90% TFA-H2O:acetonitrile)
Sources & evidence
- ORD record
- ord-29ee660238c244e79204fb42c13881e0
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216998B2
Reaction notes
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