Hydrochloric Acid → 6-Cyclopentylmethyl-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 68932노트

반응식

HRID 68932 반응식
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].[CH:18]1([CH2:23][C:24](OC)=O)[CH2:22][CH2:21][CH2:20][CH2:19]1.[H-].[Na+].Cl>C(O)C>[CH:18]1([CH2:23][C:24]2[NH:17][C:15](=[O:16])[C:3]3[CH:4]=[N:5][N:6]([C:7]4[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=4[CH3:14])[C:2]=3[N:1]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 121505615-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamideHCID 12512040Methyl 2-cyclopentylacetate

생성물 1

HCID 1360351316-Cyclopentylmethyl-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

0.1 g (0.43 mmol) of 5-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide (Example 15A) is dissolved under argon in 6 ml of absolute ethanol and 0.24 g (1.7 mmol) of methyl cyclopentylacetate and 0.17 g (4.34 mmol) of 60% sodium hydride (suspension in mineral oil) are added. The reaction mixture is heated to reflux overnight. Cooling to room temperature is followed by acidification with concentrated hydrochloric acid. The sodium chloride precipitated thereby is filtered off. The filtrate is concentrated in vacuo, and the remaining residue is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 74 mg (53% of theory) of the product are obtained as a colourless solid.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customThe sodium chloride precipitated
  4. filtrationthereby is filtered off
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe remaining residue is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  7. custom74 mg (53% of theory) of the product are obtained as a colourless solid

출처 및 근거

ORD 기록
ord-0a9229a052a948f3ad706aee8a3c9596
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822479B2

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