Water → 7-Nitro-5-oxo-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide

HRID 64350Notes

Reaction equation

[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[C:3]=1[C:20]([NH2:22])=[O:21].Cl[C:24]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:25]=1[C:26](OC)=[O:27].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N+:34]([C:31]1[CH:30]=[C:25]2[C:24](=[CH:33][CH:32]=1)[N:6]1[N:5]=[C:4]([C:7]3[CH:8]=[CH:9][C:10]([O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:11][CH:12]=3)[C:3]([C:20]([NH2:22])=[O:21])=[C:2]1[NH:1][C:26]2=[O:27])([O-:36])=[O:35]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (220 mg, 0.75 mmol), methyl 2-chloro-5-nitrobenzoate (160 mg, 0.75 mmol) and K2CO3 (155 mg, 1.13 mmol) in DMF (10 mL) was heated to 80° C. for 16 hr under N2. The reaction was poured into water (30 ml), and extracted with ethyl acetate (20 mL×3). The combined organic layers were dried over Na2SO4, concentrated under reduced pressure to a residue, which was purified by a silica gel column eluting with 10% to 50% EA in PE to afford 85 mg (27.3%) of 7-nitro-5-oxo-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide as a yellow solid. MS (ESI, m/e) [M+1]+ 442.1.

Workup

extractionextracted with ethyl acetate (20 mL×3)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated under reduced pressure to a residue, which
customwas purified by a silica gel column
washeluting with 10% to 50% EA in PE

Sources & evidence

ORD record: ord-d11019a6bfe349dd90c1e6964d5e2530
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447106B2

Reaction notes

Loading…