Potassium Carbonate → HCID 86658107, compound

HRID 245502Notes

Reaction equation

HRID 245502 reaction equation
[Cl:1][C:2]1[C:3]([C:8](=[N:27][OH:28])[C:9]2[C:10](F)=[C:11]([F:25])[C:12]([N:17]3[CH2:22][C@H:21]([CH3:23])[O:20][C@H:19]([CH3:24])[CH2:18]3)=[C:13]([CH2:15][OH:16])[CH:14]=2)=[N:4][CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[Cl:1][C:2]1[C:3]([C:8]2[C:9]3[CH:14]=[C:13]([CH2:15][OH:16])[C:12]([N:17]4[CH2:22][C@H:21]([CH3:23])[O:20][C@H:19]([CH3:24])[CH2:18]4)=[C:11]([F:25])[C:10]=3[O:28][N:27]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 136360835HCID 136360835, compound2×

Product 1

HCID 86658107HCID 86658107, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

{5-[(3-chloropyrazin-2-yl)(hydroxyimino)methyl]-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3,4-difluorophenyl}methanol (Intermediate 198, 106 mg, 0.26 mmol) in MeCN (4 mL) was treated with K2CO3 (53.2 mg, 0.39 mmol) at 120° C. for 1 hr. The mixture was diluted with EtOAc and washed with water and brine. The EtOAc solution was dried over anhydrous sodium sulfate, filtered and concentrated to afford 90 mg of product.

Workup

  1. washwashed with water and brine
  2. dry with materialThe EtOAc solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1a2fc5a40c14a99ae870d0b1c1a5eed
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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