Dimethylcarbamoyl Chloride → HCID 15027398, compound

HRID 1461447Notes

Reaction equation

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

Participants

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride

HCID 517045Sodium Acetate

HCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

HCID 15027398HCID 15027398, compoundYield 30%

Procedure

According to the procedure of Example 62, 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine is reacted with 14 eq of dimethylcarbamoyl chloride and 3.5 eq of sodium acetate (added in portions). The crude product is purified by column chromatography (silica gel, 1:4/ethyl acetate:methylene chloride). Recrystallization from methylene chloride:hexane, followed by column chromatography (silica gel, ether) and recrystallization from methanol:water gives pure 1-(4-chlorobenzoyl)-N-[(dimethylamino)carbonyl]-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine (30%); mp 173°-174° C.

Workup

customThe crude product is purified by column chromatography (silica gel, 1:4/ethyl acetate:methylene chloride)
customRecrystallization from methylene chloride
customhexane, followed by column chromatography (silica gel, ether) and recrystallization from methanol

Sources & evidence

ORD record: ord-0e5ddeee52bc445f85b50095c41325dc
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075330

Reaction notes

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