Thionyl Chloride → 6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide

HRID 1505725Notes

Reaction equation

HRID 1505725 reaction equation
O[C:2]1([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:10]=[C:9]2[CH2:11][NH:12][CH:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[CH2:14][N:7]3[C:8]2=[C:4]([CH:5]=[CH:6]3)[CH:3]1[C:24]([F:27])([F:26])[F:25].S(Cl)(Cl)=O>N1C=CC=CC=1>[CH2:28]([C:2]1[C:3]([C:24]([F:26])([F:27])[F:25])=[C:4]2[C:8]3=[C:9]([CH2:11][NH:12][CH:13]([C:15]([NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[O:16])[CH2:14][N:7]3[CH:6]=[CH:5]2)[CH:10]=1)[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 866919946-hydroxy-6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide

Product 1

HCID 866919956-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 6-hydroxy-6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide was further processed with thionyl chloride and pyridine as described in Example 1, above to yield 6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide (5 mg).

Sources & evidence

ORD record
ord-54abc5c103384408876e879736eb4131
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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