Chloride → 7-Chloro-4-[3-(5-cyclopropylaminomethyl-[1,2,4]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1266882Notes

Reaction equation

HRID 1266882 reaction equation
[Cl:1][C:2]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][C:5]2[NH:6][C:7](=[O:24])[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]4[C:21]([CH2:22]O)=[N:20][CH:19]=[N:18]4)[CH:12]=3)=[N:10][C:4]=2[CH:3]=1.S(Cl)(Cl)=O.[Cl-].[CH:36]1([NH2:39])[CH2:38][CH2:37]1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[C:26]([C:27]([F:28])([F:29])[F:30])=[CH:25][C:5]2[NH:6][C:7](=[O:24])[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]4[C:21]([CH2:22][NH:39][CH:36]5[CH2:38][CH2:37]5)=[N:20][CH:19]=[N:18]4)[CH:12]=3)=[N:10][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 185487877-Chloro-4-[3-(5-hydroxymethyl-[1,2,4]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 185488777-Chloro-4-[3-(5-cyclopropylaminomethyl-[1,2,4]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 7-chloro-4-[3-(5-hydroxymethyl-[1,2,4]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 63) (218 mg, 0.50 mmol) by reaction with thionylchloride in dichloromethane and subsequent treatment of the corresponding chloride with cyclopropylamine in DMF as described in Example 47. Obtained as an off-white solid (135 mg, 57%).

Sources & evidence

ORD record
ord-83f4f2ffae0641609f26f14733dfac55
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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