Sodium Chloride → HCID 10143559, compound

HRID 1635580Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([N:14]([CH2:20][C:21]1[NH:22][C:23]([CH3:27])=[C:24]([CH3:26])[N:25]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13].Cl[CH2:29][C:30]#[N:31].[C:32]([O-:35])([O-])=O.[K+].[K+].[Na+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([N:14]([CH2:20][C:21]1[N:25]([CH2:5][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:32]=2[O:35][CH2:29][C:30]#[N:31])[C:24]([CH3:26])=[C:23]([CH3:27])[N:22]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13]

Participants

Conditions

Temperature: 22 °C

Procedure

A mixture of 250 mg (0.50 mmol) of (2-chloro-3,4-dimethoxyphenyl)-N-(4,5-dimethylimidazol-2-yl)methyl-N-(3-methylbutyl)carboxamide, 52 μL of chloroacetonitrile (0.75 mmol), 276 mg (2.0 mmol) of K2CO3, and 3 mL of anhydrous DMF is stirred under nitrogen at 22° C. for 24 h and poured into 10% NaCl. The mixture is extracted with 20 mL of ethyl acetate. The extract is concentrated under reduced pressure, diluted with 20 mL of xylenes, and the volatiles are thoroughly evaporated. The crude product is purified by chromatography on 30 g of silica gel using chloroform—methanol—28% ammonium hydroxide (98:1.8:0.2, v/v/v) for elution to afford 113 mg (42% yield) of the title compound. Mass Spec m/z (M++1) 539.

Workup

extractionThe mixture is extracted with 20 mL of ethyl acetate
concentrationThe extract is concentrated under reduced pressure
additiondiluted with 20 mL of xylenes
customthe volatiles are thoroughly evaporated
customThe crude product is purified by chromatography on 30 g of silica gel
washfor elution

Sources & evidence

ORD record: ord-5538d297ad904fafa9aa317f41d0d00a
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509366B2

Reaction notes

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