Methanol → HCID 69417510, compound

HRID 916970Notes

Reaction equation

HRID 916970 reaction equation
[H-].[Na+].CO.[C:5]([CH2:7][C:8]([NH2:10])=[O:9])#[N:6].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19](=O)[C:20]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)=[CH:21]N(C)C>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1[NH:10][C:8](=[O:9])[C:7]([C:5]#[N:6])=[CH:21][C:20]=1[C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 69418376HCID 69418376, compound

Product 1

HCID 69417510HCID 69417510, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
95 °C

Procedure

To a dried round bottom flask was added NaH (3.73 g in 60% disp.; 93.3 mmol), DMF (100 mL), and methanol (3.78 mL; 93.3 mmol) under a nitrogen atmosphere. To this suspension was added a solution of 2-cyanoacetamide (3.92 g; 46.6 mmol) in DMF (30 mL) via syringe. Then a solution of the crude product of Step B (42.4 mmol) in DMF (30 mL) was added via syringe. The resulting reaction mixture was heated to 95° C. and stirred for 3 hours. The reaction was quenched with saturated aq. NaHSO4 solution and extracted with methylene chloride (3×). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by trituration in ethanol. The precipitate was collected and washed with cold ethanol to afford the desired product: m/e=355 (M+1) Rt=3.3 min on LCMS.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with saturated aq. NaHSO4 solution
  3. extractionextracted with methylene chloride (3×)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. customThe precipitate was collected
  9. washwashed with cold ethanol

Sources & evidence

ORD record
ord-563825c5be8741e4855e7d594d9c08ae
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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