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 64348노트

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HRID 64348 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67451325Methyl 2-(2-fluoro-5-nitrophenyl)acetateHCID 178513497HCID 178513497, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-53bad647ea004ddea9e21e0dbd491a2c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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