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

HRID 68932ノート

反応式

HRID 68932 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a9229a052a948f3ad706aee8a3c9596
出典データセット
uspto-grants-2014_09
特許番号
US08822479B2

反応ノート

読み込み中…