Water → HCID 21254753, compound

HRID 850170Notes

Reaction equation

[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:30])=[C:23]([CH2:28]O)[C:24]([Cl:27])=[CH:25][CH:26]=2)[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.CS([Cl:42])(=O)=O.O>CN(C)C=O>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:30])=[C:23]([C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:28][Cl:42])[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-[N-[(E)-3-(6-Acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-hydroxymethyl-2,6-dichlorobenzene (5.36 g) was dissolved in N,N-dimethylformamide (30 ml) under nitrogen atmosphere, triethylamine (2.4 g) and methanesulfonyl chloride (1.3 ml) were added to the mixture at 0° C., and the mixture was stirred at 0° C. for 1 hour and at ambient temperature for 18 hours. The reaction mixture was poured into water and extracted with chloroform. The organic layer was separated, washed with saturated aqueous solution of sodium hydrogen carbonate and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with ethyl acetate to give 3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyl chloride (5-1 g) as a powder.

Workup

extractionextracted with chloroform
customThe organic layer was separated
washwashed with saturated aqueous solution of sodium hydrogen carbonate and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
washThe residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-0b780e75326141adbe166c94f4a0b1a1
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015818

Reaction notes

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