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

HRID 498834Notes

Reaction equation

HRID 498834 reaction equation
[Cl:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([CH2:24]O)[CH:19]=4)[CH:13]=3)[CH2:9][C:8](=[O:26])[NH:7][C:6]=2[CH:27]=1.S(Cl)(Cl)=O.[Cl-].[CH:34]1([NH2:37])[CH2:36][CH2:35]1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][NH:37][CH:34]5[CH2:36][CH2:35]5)[CH:19]=4)[CH:13]=3)[CH2:9][C:8](=[O:26])[NH:7][C:6]=2[CH:27]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 223177268-Chloro-4-[3-(2-hydroxymethyl-pyridin-4-yl)-phenyl]-7-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 223175628-Chloro-4-[3-(2-cyclopropylaminomethyl-pyridin-4-yl)-phenyl]-7-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 8-chloro-4-[3-(2-hydroxymethyl-pyridin-4-yl)-phenyl]-7-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 282) (196 mg, 0.50 mmol) by reaction with thionylchloride in CH2Cl2 and subsequent treatment of the corresponding crude chloride with cyclopropylamine in DMF according to the general procedure of example 288. Obtained as a light brown (96 mg, 45%).

Workup

  1. customObtained as a light brown (96 mg, 45%)

Sources & evidence

ORD record
ord-ddbba3d89304485fab35674ccfc5c45b
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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