Hydroxyamine hydrochloride → 2-(5-aminothiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1170929Notes

Reaction equation

CC1[N:3]([C:8]2[S:12][CH:11]=[N:10][C:9]=2[C:13]2[N:14]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:15](=[O:27])[C:16]3[C:22]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:20]=[CH:19][C:17]=3[N:18]=2)C(C)=CC=1.Cl.NO>C(O)C>[NH2:3][C:8]1[S:12][CH:11]=[N:10][C:9]=1[C:13]1[N:14]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:15](=[O:27])[C:16]2[C:22]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one (7 mg, 0.014 mmol) in ethanol was added hydroxylamine hydrochloride (9.82 mg, 0.14 mmol) and the mixture was heated up to 80° C. for 60 hours. The reaction was then concentrated and purified with flash chromatography providing an off-white solid (1.5 mg). 1H NMR (400 MHz, CDCl3) δ 8.72 (d, 1H), 8.02 (s, 1H), 7.52 (d, 1H), 7.30 (m, 5H), 6.93 (s, br, 2H), 4.89 (t, 2H), 3.17 (t, 2H). MS m/z 418.3 (M+H)+.

Workup

concentrationThe reaction was then concentrated
custompurified with flash chromatography

Sources & evidence

ORD record: ord-b4e2690d4d7749ac99e02ae3c6f6b95a
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829572B2

Reaction notes

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