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

HRID 1265888Notes

Reaction equation

HRID 1265888 reaction equation
OC[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(N)[CH2:40][CH2:39]1.[CH3:42][N:43](C=O)C>ClCCl>[CH:38]1([NH:5][CH2:4][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]=[CH:42][N:43]=2)[CH2:40][CH2:39]1

Participants

7

Reactant 5

HCID 312ChlorideHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 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 186134444-[3-(5-Cyclopropylaminomethyl-[1,2,4]triazol-1-yl)-phenyl]-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 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) (180 mg, 0.42 mmol) by reaction with thionylchloride in dichloromethane and subsequent treatment of the corresponding chloride with cyclopropylamine in DMF according to the method described in Example 45. Obtained as a light yellow solid (108 mg, 55%).

Sources & evidence

ORD record
ord-31e67bcffdf8480bb67686c1eb758f67
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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