Water → HCID 59718926, compound

HRID 1852544Notes

Reaction equation

HRID 1852544 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.[N:13]1([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([CH2:35][OH:36])[CH2:31][CH2:30]3)[N:23]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1.O.CCOC(C)=O>CS(C)=O>[N:13]1([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH:29]3[CH2:30][CH2:31][CH:32]([CH:35]=[O:36])[CH2:33][CH2:34]3)[N:23]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 1087942-Iodoxybenzoic acid2×HCID 178520972HCID 178520972, compound

Product 1

HCID 59718926HCID 59718926, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Iodoxybenzoic acid (830 mg, 2.96 mmol) was added to a solution of trans-[4-(4-benzo-triazol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanol (640 mg, 1.97 mmol) in DMSO (10 mL) and the resulting mixture was stirred at RT for 23 hours. An additional aliquot of o-iodoxy-benzoic acid (830 mg, 2.96 mmol) was then added. After a few hours, the reaction was stopped. Water was added and the resulting mixture was stirred for 20 minutes, the solid formed was filtered and the filtrate was extracted 3 times with EtOAc. The combined organic extracts were washed once with water, dried over Na2SO4 and filtered; the solvent was evaporated under reduced pressure. The white solid formed was washed several times with EtOAc and it was combined with the previous obtained solid to give 789 mg of crude residue. This crude material was purified via flash chromatography (heptane/EtOAc, with a gradient from 20% to 50% of EtOAc) to give 452 mg (70% yield) of 4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclo-hexanecarbaldehyde.

Workup

  1. waitAfter a few hours
  2. stirringthe resulting mixture was stirred for 20 minutes
  3. customthe solid formed
  4. filtrationwas filtered
  5. extractionthe filtrate was extracted 3 times with EtOAc
  6. washThe combined organic extracts were washed once with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customThe white solid formed
  11. washwas washed several times with EtOAc and it
  12. customprevious obtained solid
  13. customto give 789 mg of crude residue
  14. customThis crude material was purified via flash chromatography (heptane/EtOAc

Sources & evidence

ORD record
ord-9c9e7bb40b18400ea1dcd50298493214
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

Loading…