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

HRID 1265874Notes

Reaction equation

HRID 1265874 reaction equation
[Cl:1][C:2]1[C:3]([N:27]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]4[C:22]([CH2:23]O)=[CH:21][N:20]=[N:19]4)[CH:13]=3)[CH2:9][C:8](=[O:25])[NH:7][C:6]=2[CH:26]=1.S(Cl)(Cl)=O.[Cl-].[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[C:3]([N:27]([CH2:29][CH:30]([CH3:31])[CH3:32])[CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]4[C:22]([CH2:23][N:38]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]5)=[CH:21][N:20]=[N:19]4)[CH:13]=3)[CH2:9][C:8](=[O:25])[NH:7][C:6]=2[CH:26]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 18613355HCID 18613355, compound

Product 1

HCID 101649308-Chloro-7-(isobutyl-methyl-amino)-4-[3-(5-piperidin-1-ylmethyl-[1,2,3]triazol-1-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 8-chloro-4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-7-(isobutyl-methyl-amino)-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 101) (220 mg, 0.49 mmol) by reaction with thionylchloride in dichloromethane and subsequent treatment of the corresponding chloride with piperidine in DMF according to the method described in Example 45. Obtained as a light brown solid (250 mg, 99%).

Sources & evidence

ORD record
ord-266e38ed030143b8a2c6905a8edb662b
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

Loading…