Methyl iodide → HCID 58229861, compound

HRID 221992Notes

Reaction equation

HRID 221992 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]([NH:5][C:6]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:13][CH:12]=2)[CH2:9][CH:8]([OH:10])[CH2:7]1)=[O:4].IC.[C:46]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:43][C:2]([F:42])([F:1])[C:3]([N:5]([C:6]1([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)[CH2:9][CH:8]([OH:10])[CH2:7]1)[CH3:46])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 44556080HCID 44556080, compound

Product 1

HCID 58229861HCID 58229861, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,2,2-trifluoro-N-(3-hydroxy-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-3) (16 mg, 0.043 mmol), iodomethane (0.0034 mL, 0.055 mmol), and K2CO3 (7.6 mg, 0.055 mmol) in DMF (1 mL) was stirred at room temperature for 1 hour. The mixture was quenched with water, extracted with EtOAc, washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to give 2,2,2-trifluoro-N-(3-hydroxy-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)-N-methylacetamide (4-8).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15d6a69ed9ac4ee684c81aa526834681
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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