Potassium Carbonate → HCID 67358607, compound

HRID 577958Notes

Reaction equation

HRID 577958 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:21]([N:38]2[CH2:43][C@H:42]([CH3:44])[O:41][C@H:40]([CH3:45])[CH2:39]2)=[C:22]([F:37])[C:23](F)=[C:24]([C:26]([C:29]2[CH:34]=[N:33][C:32](Cl)=[CH:31][N:30]=2)=[N:27][OH:28])[CH:25]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:46][S-:47].[Na+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OC(=O)C)C>[CH3:44][C@@H:42]1[CH2:43][N:38]([C:21]2[C:20]([CH2:19][OH:18])=[CH:25][C:24]3[C:26]([C:29]4[CH:34]=[N:33][C:32]([S:47][CH3:46])=[CH:31][N:30]=4)=[N:27][O:28][C:23]=3[C:22]=2[F:37])[CH2:39][C@H:40]([CH3:45])[O:41]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4378561Sodium methanethiolateHCID 136360822HCID 136360822, compound2×

Product 1

HCID 67358607HCID 67358607, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-{5-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}-1-(5-chloropyrazin-2-yl)-N-hydroxymethanimine (Intermediate 200, 400 mg, 0.61 mmol) in DMF (5 mL) was treated with sodium thiomethoxide (45.3 mg, 0.61 mmol) at room temperature, the mixture was stirred at room temperature for 10 min. K2CO3 (5 eq) was added and the mixture was heated to 100° C. for 1 hour. The reaction mixture was diluted with ethylacetate (20 ml). Organic layer washed with water and brine, then dried over sodium sulfate, filtered, and the filtrate was concentrated, purified by silica gel column chromatography (Hexanses/EtOAc, gradient) to give the desired product (97 mg, 39.0%).

Workup

  1. temperaturethe mixture was heated to 100° C. for 1 hour
  2. washOrganic layer washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. custompurified by silica gel column chromatography (Hexanses/EtOAc, gradient)

Sources & evidence

ORD record
ord-7c2a426f9409446fbbd82b3605cbb6fc
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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