Methyl 1-methylhydrazinecarboxylate → HCID 59355477, compound

HRID 887716Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[O:15][C:16](=[O:26])[C:17]3[N:23]=[C:22]([Cl:24])[CH:21]=[C:20]([CH3:25])[C:18]=3[N:19]=2)[N:5]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[N:6]=1.[CH3:27][O:28][C:29]([N:31]([CH3:33])[NH2:32])=[O:30]>CN(C=O)C>[CH3:27][O:28][C:29]([N:31]([CH3:33])[NH:32][C:16]([C:17]1[C:18]([NH:19][C:14]([C:4]2[N:5]([C:7]3[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]=3)[N:6]=[C:2]([Br:1])[CH:3]=2)=[O:15])=[C:20]([CH3:25])[CH:21]=[C:22]([Cl:24])[N:23]=1)=[O:26])=[O:30]

Participants

Conditions

Temperature: 80 °C

Procedure

2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one (140 mg) (example 7, step 4) was dissolved in DMF (10 mL) and N-methyl-hydrazinecarboxylic acid methyl ester (161 mg) was added. The solution was stirred for 3 hours at 80° C., then 12 hours at room temperature and again for 3.5 hours at 80° C. The reaction mixture was quenched was diluted with MTB-ether and washed 4× with water, washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (hexane/ethyl acetate=2:1, then 1.5:1, Rf=0.15 in hexane/ethyl acetate=2:1) to afford 112 mg of compound 8 of the present invention of the formula

Workup

wait12 hours at room temperature and again for 3.5 hours at 80° C
customThe reaction mixture was quenched
additionwas diluted with MTB-ether
washwashed 4× with water
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuum
customThe residue was purified by column chromatography (hexane/ethyl acetate=2:1

Sources & evidence

ORD record: ord-b296a78f87554c1986c54f01bb070dfc
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247431B2

Reaction notes

Loading…