Dimethyl Sulfoxide → HCID 136338084, compound

HRID 629046Notes

Reaction equation

C(=O)([O-])O.[Na+].CS(C)=O.Cl.[NH2:11][OH:12].[CH2:13]([O:15][C:16]1[CH:17]=[N:18][C:19]([N:22]2[C:27](=[O:28])[C:26]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([C:36]4[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=4[C:38]#[N:39])=[N:34][CH:35]=3)=[C:25]([CH2:44][CH2:45][CH3:46])[N:24]=[C:23]2[CH:47]([CH3:49])[CH3:48])=[N:20][CH:21]=1)[CH3:14]>C(OCC)(=O)C.O>[CH2:13]([O:15][C:16]1[CH:17]=[N:18][C:19]([N:22]2[C:27](=[O:28])[C:26]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([C:36]4[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=4[C:38](=[N:11][OH:12])[NH2:39])=[N:34][CH:35]=3)=[C:25]([CH2:44][CH2:45][CH3:46])[N:24]=[C:23]2[CH:47]([CH3:49])[CH3:48])=[N:20][CH:21]=1)[CH3:14]

Participants

Conditions

Temperature: 40 °C

Procedure

Process 5: Sodium hydrogen carbonate (1.19 g, 14.1 mmol) was added to dimethyl sulfoxide (15 mL) mixture of hydroxylamine hydrochloride (838 mg, 12.1 mmol) and stirred for 1 hour at 40° C. The reaction mixture was added dimethyl sulfoxide (15 mL) solution of 2-{5-{[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile (353 mg, 0.71 mmol) and stirred for 18 hours at 90° C. The reaction mixture was added water (80 mL) and ethyl acetate (20 mL) and stirred for 30 minutes. The precipitated solid was collected by filtration and washed with water and ethyl acetate. It was then dried in vacuo to give 2-{5-{[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}-N′-hydroxybenzimidamide (214 mg, 57%) as a white solid.

Workup

stirringstirred for 18 hours at 90° C
stirringstirred for 30 minutes
filtrationThe precipitated solid was collected by filtration
washwashed with water and ethyl acetate
customIt was then dried in vacuo

Sources & evidence

ORD record: ord-f94634d618e24e989e59ef073c0a1852
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315493B2

Reaction notes

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