Chloride → 4-(3-{5-[(Cyclopropylmethyl-amino)-methyl]-[1,2,3]triazol-1-yl}-phenyl)-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265873Notes

Reaction equation

HRID 1265873 reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([CH3:32])[C:24]([N:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:27])=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[N:6]=[N:5][CH:4]=1.S(Cl)(Cl)=O.[Cl-].[CH:38]1([CH2:41][NH2:42])[CH2:40][CH2:39]1>ClCCl.CN(C=O)C>[CH:38]1([CH2:41][NH:42][CH2:2][C:3]2[N:7]([C:8]3[CH:9]=[C:10]([C:14]4[CH2:20][C:19](=[O:21])[NH:18][C:17]5[CH:22]=[C:23]([CH3:32])[C:24]([N:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:27])=[CH:25][C:16]=5[N:15]=4)[CH:11]=[CH:12][CH:13]=3)[N:6]=[N:5][CH:4]=2)[CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 75646CyclopropanemethanamineHCID 186131914-[3-(5-Hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 101631704-(3-{5-[(Cyclopropylmethyl-amino)-methyl]-[1,2,3]triazol-1-yl}-phenyl)-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 132) (250 mg, 0.58 mmol) by reaction with thionylchloride in dichloromethane and subsequent treatment of the corresponding chloride with cyclopropylmethylamine in DMF according to the method described in Example 45. Obtained as a light yellow solid (50 mg, 18%).

Sources & evidence

ORD record
ord-55731a642c53477897ddb6d42bc0ffe7
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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