Dimethylcarbamoyl Chloride → N,N-dimethyl-4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxamide hydrochloride

HRID 1809655Notes

Reaction equation

[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:34][N:35]([CH3:39])[C:36]([Cl:38])=[O:37]>>[ClH:38].[CH3:34][N:35]([CH3:39])[C:36]([N:31]1[CH2:32][CH2:33][CH:28]([C:25]2[N:24]=[C:23]([NH:22][C:10]3[C:9]([O:8][C:7]4[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=4)=[CH:14][C:13]([S:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)=[CH:12][N:11]=3)[S:27][N:26]=2)[CH2:29][CH2:30]1)=[O:37]

Participants

Reactant 2

HCID 6598Dimethylcarbamoyl Chloride

HCID 67487355N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(piperidin-4-yl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 67487750N,N-dimethyl-4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxamide hydrochlorideYield 79.01%

Procedure

Following the procedure in Example 1, Step G, and using N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(piperidin-4-yl)-1,2,4-thiadiazol-5-amine (150 mg, 0.3141 mmol) and dimethylcarbamic chloride (33.77 mg, 0.3141 mmol) provided N,N-dimethyl-4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxamide hydrochloride (145.2 mg, 0.2481 mmol, 79.01% yield). Mass spectrum (apci) m/z=549.1 (M+H—HCl).

Sources & evidence

ORD record: ord-132db0d1654548129be9d25a02e01af9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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