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

HRID 237892Notes

Reaction equation

HRID 237892 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 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-fc65be464776411697a6f5ca1959d8e0
Source dataset
uspto-grants-2014_02
Patent number
US08642605B2

Reaction notes

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