Methyl iodide → HCID 131735918, compound

HRID 2207427Notes

Reaction equation

HRID 2207427 reaction equation
[F:1][C:2]([F:34])([CH:8]([OH:33])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([NH:21][C:22]3[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][N:23]=3)[CH:18]=[C:17]([CH3:32])[CH:16]=2)=[CH:11][N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1CCN2C(=NCCC2)CC1.[C:46](=[S:48])=[S:47].[CH3:49]I>O.CN(C=O)C>[F:34][C:2]([F:1])([CH:8]([O:33][C:46]([S:48][CH3:49])=[S:47])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([NH:21][C:22]3[N:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[CH:24][N:23]=3)[CH:18]=[C:17]([CH3:32])[CH:16]=2)=[CH:11][N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 118093050HCID 118093050, compound

Product 1

HCID 131735918HCID 131735918, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2,2-difluoro-3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate (86.9 mg, 0.180 mmol), anhydrous DMF (1.00 mL), DBU (0.170 mL, 1.13 mmol) and CS2 (0.110 mL, 1.83 mmol) was stirred at room temperature for 1 hour under Ar(g). Methyliodide (0.110 mL, 1.76 mmol) was added to the reaction mixture and t stirred for 45 minutes at room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (20% ethyl acetate in hexanes) to afford ethyl 2,2-difluoro-3-{[(methylsulfanyl)carbonothioyl]oxy}-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate. MS APCI C24H22F5N4O3S2 [M+H]+ 573. found 573.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6f6b56e642e04fbea67db869347dc1c2
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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