4-Aminocyclohexanol → HCID 178521588, compound

HRID 1483815Notes

Reaction equation

HRID 1483815 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[C:4]2[N:3]=1.[NH2:21][CH:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1.CCN(C(C)C)C(C)C>CC(O)C.C([O-])(O)=O.[Na+]>[F:18][C:17]([F:20])([F:19])[C:13]1[CH:12]=[C:11]([C:10]2[CH:9]=[N:8][N:5]3[CH:6]=[CH:7][C:2]([NH:21][C@H:22]4[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]4)=[N:3][C:4]=23)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 812934-AminocyclohexanolHCID 81531DiisopropylethylamineHCID 59662442HCID 59662442, compound

Product 1

HCID 178521588HCID 178521588, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5-chloro-3-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine (100 mg, 0.336 mmol), 4-aminocyclohexanol (58.0 mg, 0.504 mmol), and DIEA (0.117 ml, 0.672 mmol) in 2-propanol (3 ml) was irradiated to 135° C. for 14 h in a Biotage microwave. After cooling, the mixture was diluted with saturated aqueous NaHCO3, and extracted three times with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. After absorbing on celite, the compound was purified by Isco (12 g silica, 1/5/4 MeOH/EtOAc/hex) to give trans-4-((3-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanol (101 mg, 80% yield) as a white solid.

Workup

  1. customwas irradiated to 135° C. for 14 h in a Biotage microwave
  2. temperatureAfter cooling
  3. extractionextracted three times with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customAfter absorbing on celite
  8. customthe compound was purified by Isco (12 g silica, 1/5/4 MeOH/EtOAc/hex)

Sources & evidence

ORD record
ord-1a6d20efe06844858f67649ddb774a86
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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