Ethyl Acetate → HCID 86686798, compound

HRID 1403158Notes

Reaction equation

HRID 1403158 reaction equation
[F:1][CH:2]([F:38])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([O:20][CH:21]3[CH2:24][N:23]([C:25]([C@H:27]4[CH2:32][CH2:31][C@@H:30]([OH:33])[CH2:29][CH2:28]4)=[O:26])[CH2:22]3)[CH:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=2[N:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C>C(Cl)Cl>[F:38][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([O:20][CH:21]3[CH2:22][N:23]([C:25]([CH:27]4[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]4)=[O:26])[CH2:24]3)[CH:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 178520991HCID 178520991, compound

Product 1

HCID 86686798HCID 86686798, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)azetidin-1-yl](cis-4-hydroxycyclohexyl)methanone (60 mg) in methylene chloride (1.2 mL) was added a Dess-Martin reagent (53 mg) under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture were added ethyl acetate and a saturated aqueous sodium bicarbonate solution, the organic layer was extracted, washed with saturated brine, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0-90:10) to obtain 4-{[3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)azetidin-1-yl]carbonyl}cyclohexanone (20 mg).

Workup

  1. temperaturecooling
  2. extractiona saturated aqueous sodium bicarbonate solution, the organic layer was extracted
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0-90:10)

Sources & evidence

ORD record
ord-47dc84e22fc9425191c392f43f7891ab
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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