Butyryl chloride → HCID 59656379, compound

HRID 561307Notes

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.[C:30](Cl)(=[O:34])[CH2:31][CH2:32][CH3:33].[Cl:36]C(OCC)=O>>[Cl:36][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20](=[O:29])(=[O:28])[NH:21][CH:22]2[CH2:23][CH2:24][N:25]([C:30](=[O:34])[CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27]2)=[CH:12][CH:11]=1)=[O:9]

Participants

Reactant 3

HCID 8855Butyryl chloride

HCID 10928Ethyl chloroformate

HCID 11750377HCID 11750377, compound

Product 1

HCID 59656379HCID 59656379, 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 butyryl chloride for ethyl chlorformate. Wt.: 21 mg (27%). 1H NMR (300 MHz, CDCl3) δ 8.67 (m, 2H), 8.48 (d, 1H), 8.35 (d, 1H), 8.20 (s, 1H), 7.82 (d, 1H), 7.72 (m, 2H), 7.41 (m, 2H), 7.09 (m, 1H), 4.78 (d, 1H), 4.31 (m, 1H), 3.67 (m, 1H), 3.35 (m, 1H), 2.95 (m, 1H), 2.22 (m, 2H), 1.60 (4H), 1.27 (m, 2H), 0.92 (t, 3H); LC/MS m/z 515 (M+H)+.

Sources & evidence

ORD record: ord-0dc7b8868a9045aa9a33fa7065854f05
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063222B2

Reaction notes

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