Water → HCID 178521605, compound

HRID 1852534Notes

Reaction equation

HRID 1852534 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[N:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O.O.CCO[C:24]([CH3:26])=[O:25]>CN1C(=O)CCC1>[N:11]1([C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:11][C@H:15]3[CH2:16][CH2:26][C@H:24]([OH:25])[CH2:19][CH2:14]3)[N:10]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 59718913HCID 59718913, compound

Product 1

HCID 178521605HCID 178521605, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(2-methanesulfonyl-pyrimidin-4-yl)-1H-benzotriazole (1.59 g, 6 mmol) in 15 mL of NMP was added trans-4-aminocyclohexane (3.11 g, 27 mmol) and the resulting mixture was stirred at 120° C. for 2 hours. It was then cooled, poured onto 100 mL of water, stirred and allowed to stand overnight. The resulting suspension was filtered, the collected solids were washed with water and dissolved with CH2Cl2; the solvent was removed under reduced pressure. The solid residue formed was taken up with EtOAc, filtered and dried to give trans-4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexanol as a white solid (910 mg, 51% yield), mp=224.8-228.1° C.; MS=311 (M+H)+.

Workup

  1. temperatureIt was then cooled
  2. stirringstirred
  3. waitto stand overnight
  4. filtrationThe resulting suspension was filtered
  5. washthe collected solids were washed with water
  6. dissolutiondissolved with CH2Cl2
  7. customthe solvent was removed under reduced pressure
  8. customThe solid residue formed
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-7ab8f4cc28234c0ca6cf735094d32812
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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