Water → HCID 86721436, compound

HRID 869586Notes

Reaction equation

HRID 869586 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([CH2:14][C:15]3[CH:34]=[CH:33][C:18]4[C:19](=[C:29]([CH3:32])[C:30]#[N:31])[C:20]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.[CH3:35][O-:36].[Na+].O>CO>[CH:11]1([C:9]2[N:10]=[C:3]3[C:2]([O:36][CH3:35])=[N:7][CH:6]=[CH:5][N:4]3[C:8]=2[CH2:14][C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86721437HCID 86721437, compound

Product 1

HCID 86721436HCID 86721436, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Using cyclopropanecarboxyaldehyde (0.586 mL, 7.74 mmol), 3-chloropyrazin-2-amine (739 mg, 5.7 mmol) and 2-(8-ethynyl-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (1.5 g, 5.18 mmol) obtained in Reference Example 9, and in the same manner as in Reference Example 8B, 2-{8-[(8-chloro-2-cyclopropylimidazo[1,2-a]pyrazin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile was obtained. Successively, the obtained 2-{8-[(8-chloro-2-cyclopropylimidazo[1,2-a]pyrazin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile was dissolved in methanol (1 mL), 28% sodium methoxide (0.3 mL, 0.425 mmol) was added, and the mixture was stirred with heating at 60° C. Water was added to the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 v/v) to give the title compound (25 mg, 1%).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 v/v)

Sources & evidence

ORD record
ord-633395b3873145e4be8b9850fae0d65f
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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