Dimethylcarbamoyl Chloride → HCID 59656499, compound

HRID 2054867Notes

Reaction equation

[CH:1]1([NH:7][C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([S:20](=[O:29])(=[O:28])[NH:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:12][CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][N:31]([CH3:35])[C:32](Cl)=[O:33].[Cl:36]C(OCC)=O>>[CH3:30][N:31]([CH3:35])[C:32]([N:25]1[CH2:24][CH2:23][CH:22]([NH:21][S:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:36])=[CH:11][CH:12]=2)(=[O:29])=[O:28])[CH2:27][CH2:26]1)=[O:33]

Participants

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride

HCID 10928Ethyl chloroformate

HCID 11750377HCID 11750377, compound

Product 1

HCID 59656499HCID 59656499, compound

Procedure

The title compound was prepared according to the general procedure in Scheme 11, substituting 4-(piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid (2-chloro-phenyl)-amide for 4-(piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid cyclohexylamide, and dimethylcarbamyl chloride for ethyl chloroformate. Wt.: 28 mg (36%). 1H NMR (300 MHz, CDCl3) δ 8.69 (d, 1H), 8.60 (d, 1H), 8.47 (d, 1H), 8.35 (d, 1H), 8.20 (s, 1H), 7.82 (d, 1H), 7.72 (m, 2H), 7.43 (m, 2H), 7.17 (m, 1H), 4.83 (d, 1H), 3.46 (m, 2H), 3.31 (m, 1H), 2.71 (s, 6H), 2.70 (m, 2H), 1.67 (m, 2H), 1.35 (m, 2H); LC/MS m/z 516 (M+H)+.

Sources & evidence

ORD record: ord-d95e50b7ed2e4176919b39cb5ac9f8e8
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329755B2

Reaction notes

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