(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine → HCID 178433351, compound

HRID 656582Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[C:11](=S)[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[CH2:8][C:6]=2[N:7]=1.[CH3:22][C:23]1([CH3:31])[O:27][C@@H:26]([CH2:28][O:29][NH2:30])[CH2:25][O:24]1>O1CCOCC1>[CH3:22][C:23]1([CH3:31])[O:27][C@@H:26]([CH2:28][O:29]/[N:30]=[C:11]2\[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[CH2:8][C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([CH3:21])[C:5]\2=3)[CH2:25][O:24]1

Participants

Conditions

Temperature: 100 °C

Procedure

A 4 mL vial charged with (R)-2-amino-7-(2-bromo-4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-pyrido[4,3-d]pyrimidine-5-thione (31I (Example 31), 107 mg, 0.28 mmol), (R)—O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine (247 mg, 1.68 mmol), and dioxane (2 mL) was heated to 100° C. for 12 h. The crude mixture was purified by preparative reverse phase HPLC (10-70% H2O—AcCN, 0.035% TFA) to afford the product (R,Z)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one O—((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl oxime (32A) in modest yield (40 mg, 30% yield). ESI-MS: m/z 480.1 (M+H)+.

Workup

customThe crude mixture was purified by preparative reverse phase HPLC (10-70% H2O—AcCN, 0.035% TFA)

Sources & evidence

ORD record: ord-d5ba784bd1c941b6a70cf60930cb0327
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071766B2

Reaction notes

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