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

HRID 498851Notes

Reaction equation

HRID 498851 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-].[CH2:34]([NH:38][CH3:39])[CH:35]([CH3:37])[CH3:36]>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][N:38]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH3:39])[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 12249N-MethylisobutylamineHCID 24386Thionyl ChlorideHCID 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 223179648-Chloro-4-(3-{2-[(isobutyl-methyl-amino)-methyl]-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 isobutyl-methyl-amine in DMF according to the general procedure of Example 288. Obtained as a light brown solid (141 mg, 61%).

Sources & evidence

ORD record
ord-9a42dcd501ac4fa38ffc1ed706ec3d6e
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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