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2-(4-Methylcyclohexyl)acetic acid → 6-[(4-Methylcyclohexyl)methyl]-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 68935
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HRID 68935 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:5]=[CH:4][C:3]=1[C:14]([NH2:16])=[O:15].[CH3:17][CH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25](O)=O)[CH2:20][CH2:19]1.C[Si](OP(=O)=O)(C)C>O>[CH3:17][CH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25]2[NH:16][C:14](=[O:15])[C:3]3[CH:4]=[N:5][N:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[CH3:13])[C:2]=3[N:1]=2)[CH2:20][CH2:19]1
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참가 물질

5

반응물 3

HCID 36169452-(4-Methylcyclohexyl)acetic acidHCID 119839075-Amino-1-(o-tolyl)-1H-pyrazole-4-carboxamideHCID 16133246Trimethyl(phosphooxy)silane

생성물 1

HCID 1355084206-[(4-Methylcyclohexyl)methyl]-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

시약·촉매·용매 1

HCID 962Water용매

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온도
130 °C

실험 절차

150 mg (0.69 mmol) of 5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carboxamide (Example 23A) and 130 mg (0.83 mmol) of 2-(4-methylcyclohexyl)acetic acid are mixed with 0.3 ml of trimethylsilyl polyphosphate and stirred at 130° C. for 3 h. The hot reaction mixture is added to 20 ml of water and then extracted with dichloromethane (2×20 ml). The combined organic phases are washed with water (20 ml) and with saturated sodium chloride solution (20 ml) and dried over sodium sulphate. The solvent is distilled off under reduced pressure, and the crude product 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). 182 g (78% of theory) of the product are obtained.

후처리

  1. extractionextracted with dichloromethane (2×20 ml)
  2. washThe combined organic phases are washed with water (20 ml) and with saturated sodium chloride solution (20 ml)
  3. dry with materialdried over sodium sulphate
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe crude product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm
  6. custom0 min 30% B, 5 min 30% B, 50 min 95% B
  7. custom182 g (78% of theory) of the product are obtained

출처 및 근거

ORD 기록
ord-d4bbf5dfbc94414a99d88a05cef1d4c4
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822479B2

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