Potassium Carbonate → 8-Nitro-5-oxo-2-(4-phenoxyphenyl)-5,6-dihydro-4H-benzo[f]pyrazolo[1,5-a][1,3]diazepine-3-carboxamide

HRID 64348ノート

反応式

HRID 64348 の反応式
[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].C([O-])([O-])=O.[K+].[K+].F[C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=1[CH2:39][C:40](OC)=[O:41]>CN(C=O)C>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]2[N:6]3[N:5]=[C:4]([C:7]4[CH:8]=[CH:9][C:10]([O:13][C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[CH:11][CH:12]=4)[C:3]([C:20]([NH2:22])=[O:21])=[C:2]3[NH:1][C:40](=[O:41])[CH2:39][C:31]=2[CH:32]=1)([O-:38])=[O:37]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 67451325Methyl 2-(2-fluoro-5-nitrophenyl)acetateHCID 178513497HCID 178513497、化合物

生成物 1

HCID 1369281368-Nitro-5-oxo-2-(4-phenoxyphenyl)-5,6-dihydro-4H-benzo[f]pyrazolo[1,5-a][1,3]diazepine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (30 mg, 0.10 mmol) in DMF (5 mL) was added K2CO3 (28 mg, 0.20 mmol) and methyl 2-(2-fluoro-5-nitrophenyl)acetate (21 mg, 0.10 mmol). The mixture was warmed to 80° C. stirred for about 16 hr. After cooling down to RT, the mixture was concentrated under reduced pressure to remove solvent. The residue was portioned with DCM (10 mL) and water (10 mL), the aqueous was extracted with DCM (2×10 mL), the combined organic phases were washed sat. Sodium chloride (10 mL), dried over anhydrous Sodium sulfate, filtered, concentrated and purified by pre-TLC (DCM/CH3OH=20/1) got the product about 10 mg (21.9%). 1H NMR (400 MHz, DMSO-d6) δ 10.66 (br s, 1H), 8.51 (d, J=2.6 Hz, 1H), 8.37 (dd, J=2.6, 9.2 Hz, 1H), 8.07 (d, J=9.2 Hz, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.65-7.53 (br s, 2H), 7.45-7.40 (m, 2H), 7.22-7.16 (m, 1H), 7.12-7.05 (m, 4H), 3.92 (s, 2H). MS (ESI) m/e [M+1]+ 456.1.

後処理

  1. temperatureAfter cooling down to RT
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customto remove solvent
  4. extractionthe aqueous was extracted with DCM (2×10 mL)
  5. washthe combined organic phases were washed sat. Sodium chloride (10 mL)
  6. dry with materialdried over anhydrous Sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by pre-TLC (DCM/CH3OH=20/1)

出典と根拠

ORDレコード
ord-53bad647ea004ddea9e21e0dbd491a2c
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

反応ノート

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