Methanol → HCID 178508379, compound

HRID 1927248Notes

Reaction equation

HRID 1927248 reaction equation
CO.[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH:20][NH2:21])=O)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:22][C:23]1[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C[O-].[Na+].CO>C(OCC)(=O)C.O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[NH:30][C:29]([C:28]3[C:23]([NH2:22])=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:21][N:20]=2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8182592-Amino-3-cyanopyridineHCID 23694274Sodium methanolate methanolHCID 59287387(4-Benzyloxy-phenyl)-acetic acid hydrazide

Product 1

HCID 178508379HCID 178508379, compoundYield 1.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (10 mL) solution of 4-benzyloxy-phenylacetic acid hydrazide (200 mg) described in Manufacturing Example 15-1 were added 2-amino-3-cyanopyridine (92 mg) and 28% sodium methoxide-methanol solution (30 mg), which was stirred for 14 hours under heating and reflux. Water and ethyl acetate were added to the reaction solution, and then the organic layer was extracted. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate and filtered, after which the filtrate was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the titled compound (3 mg).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. extractionthe organic layer was extracted
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customafter which the filtrate was evaporated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5)

Sources & evidence

ORD record
ord-f9b378c1de824eaf995d10665e2b3265
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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