Methanol → HCID 11359162, compound

HRID 984060Notes

Reaction equation

HRID 984060 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:22])[CH:3]=1.[H-].[Na+].CO.[CH3:27][N:28](C)[CH2:29]CN>>[CH3:22][C:4]1[CH:3]=[C:2]([N:28]([CH3:29])[CH3:27])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[N:5]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 66053N,N-DimethylethylenediamineHCID 11438401HCID 11438401, compound

Product 1

HCID 11359162HCID 11359162, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 800 mg (2.5 mmol) of compound 13 and 101 mg of 60% NaH (2.5 mmol) in 5 ml N,N-dimethyl ethylendiamine was heated in a sealed tube at 120° C. for six hours. To the cooled reaction mixture was carefully added methanol to quench NaH. The resulting mixture was concentrated to dryness, and the residue was purified by flash chromatography (silica gel, 10% MeOH/CH2Cl2 with 1% NH40H) to get 100 mg of compound 14.

Workup

  1. customTo the cooled reaction mixture
  2. customto quench NaH
  3. concentrationThe resulting mixture was concentrated to dryness
  4. customthe residue was purified by flash chromatography (silica gel, 10% MeOH/CH2Cl2 with 1% NH40H)

Sources & evidence

ORD record
ord-fe4d54533af846d5818f38d24bb74f0b
Source dataset
uspto-grants-2005_03
Patent number
US06867210B2

Reaction notes

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