Dimethylcarbamoyl Chloride → HCID 59656458, compound

HRID 1726487Notes

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]C[CH2:3][CH2:2]1.[CH3:30][N:31]([CH3:35])[C:32](Cl)=[O:33].ClC(OCC)=[O:38]>>[CH3:30][N:31]([CH3:35])[C:32]([N:25]1[CH2:26][CH2:27][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][CH:1]3[CH2:6][CH2:5][O:38][CH2:3][CH2:2]3)=[CH:11][CH:12]=2)(=[O:28])=[O:29])[CH2:23][CH2:24]1)=[O:33]

Participants

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride

HCID 10928Ethyl chloroformate

HCID 11750377HCID 11750377, compound

Product 1

HCID 59656458HCID 59656458, compound

Procedure

The title compound was prepared according to the general procedure in Scheme 11, substituting 4-(piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid (tetrahydro-pyran-4-yl)-amide for 4-(piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid cyclohexylamide, and dimethylcarbamyl chloride for ethyl chloroformate. Wt.: 125 mg (78%). 1H NMR (300 MHz, CDCl3) δ 8.8.59 (m, 1H), 8.29 (m, 1H), 8.23 (d, 1H), 7.69 (m, 2H), 7.58 (d, 1H), 6.17 (d, 1H), 4.82 (d, 1H), 4.32 (m, 1H), 4.03 (m, 2H), 3.57 (m, 2H), 3.40 (m, 2H), 3.25 (m, 1H), 2.73 (s, 6H), 2.64 (m, 2H), 2.10 (m, 2H), 1.61 (m, 4H), 1.27 (m, 2H); LC/MS m/z 489 (M+H)+.

Sources & evidence

ORD record: ord-b242d47c2a1b4ff598ebbb25ac3aeba4
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491827B2

Reaction notes

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