Morpholine → HCID 178434432, compound

HRID 336860Notes

Reaction equation

HRID 336860 reaction equation
Cl[C:2]1[O:6][C:5]([C:7]2[C:12]([C:13]#[N:14])=[C:11]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[C:17]([F:22])[C:16]=3[F:23])[N:10]=[C:9]3[NH:24][N:25]=[C:26]([CH3:27])[C:8]=23)=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[CH3:27][C:26]1[C:8]2[C:9](=[N:10][C:11]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[C:17]([F:22])[C:16]=3[F:23])=[C:12]([C:13]#[N:14])[C:7]=2[C:5]2[O:6][C:2]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:3][CH:4]=2)[NH:24][N:25]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 178434430HCID 178434430, compound

Product 1

HCID 178434432HCID 178434432, compoundYield 35%

Procedure

A solution of 2.0 g (5.0 mmol) of 4-(5-chlorofuran-2-yl)-3-methyl-6-(2,3,6-trifluorophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in 11 ml of morpholine is refluxed for 20 h. The mixture is then concentrated, dissolved in dichloromethane and washed three times with 1N hydrochloric acid solution. The organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue obtained is purified by chromatography on silica (ethyl acetate gradient in dichloromethane: 10 to 20%) to give 0.76 g (35%) of 3-methyl-4-(5-morpholinofuran-2-yl)-6-(2,3,6-trifluorophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of yellow crystals.

Workup

  1. concentrationThe mixture is then concentrated
  2. dissolutiondissolved in dichloromethane
  3. washwashed three times with 1N hydrochloric acid solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customis purified by chromatography on silica (ethyl acetate gradient in dichloromethane: 10 to 20%)

Sources & evidence

ORD record
ord-f408577731b542178c21b1540a818204
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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