Hydrochloric Acid → HCID 76759376, compound

HRID 1403180Notes

Reaction equation

[F:1][C:2]1[C:3]([N:17]=[CH:18]N(C)C)=[N:4][C:5]([O:8][N:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=1.Cl.[O:23]1CCOCC1>>[F:1][C:2]1[C:3]([NH:17][CH:18]=[O:23])=[N:4][C:5]([O:8][N:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 75985010HCID 75985010, compound

Product 1

HCID 76759376HCID 76759376, compoundYield 22%

Conditions

Temperature: 23 °C

Procedure

To a suspension of N′-{5-fluoro-2-[1-phenylmethylideneaminooxy]pyrimidin-4-yl}-N,N-dimethylformamidine (0.035 g, 0.12 mmol) in dioxane (1.2 mL) was added dilute hydrochloric acid (HCl, 1 N, 0.006 g, 0.16 mmol) and the mixture was stirred at 23° C. for 16 h. The reaction mixture was purified by flash chromatography (4 g SiO2; 0→60% EtOAc/hexanes) to give N-{5-fluoro-2-[1-phenylmethylideneaminooxy]pyrimidin-4-yl}formamide (0.007 g, 22%) as a white solid: mp 210-232° C. dec; 1H NMR (400 MHz, DMSO-d6) δ 11.43 (s, 1H), 9.36 (s, 1H), 8.79 (s, 1H), 8.57 (d, J=2.4 Hz, 1H), 7.80 (dd, J=7.7, 1.6 Hz, 2H), 7.52 (m, 3H); ESIMS m/z 261 ([M+H]+), 259 ([M−H]−).

Workup

customThe reaction mixture was purified by flash chromatography (4 g SiO2; 0→60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-361e4b0c901f47be8ab6a5c72bf84d9b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912207B2

Reaction notes

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