2-(4-Methylcyclohexyl)acetic acid → HCID 135508420, compound

HRID 68935Notes

Reaction equation

HRID 68935 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 135508420HCID 135508420, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d4bbf5dfbc94414a99d88a05cef1d4c4
Source dataset
uspto-grants-2014_09
Patent number
US08822479B2

Reaction notes

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