Methanol → HCID 69417712, compound

HRID 916963Notes

Reaction equation

HRID 916963 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]([F: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]([F:31])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 69417527HCID 69417527, compound

Product 1

HCID 69417712HCID 69417712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
95 °C

Procedure

To an oven-dried round bottom flask was added 1.87 g of a 60% oil dispersion of NaH (46.8 mmol), DMF (50 mL), and methanol (1.89 mL; 46.8 mmol) under a N2 atmosphere. To this suspension was added a solution of 2-cyanoacetamide (1.97 g; 23.4 mmol) in DMF (10 mL) via syringe followed by a solution of the crude product of Step B (21.3 mmol) in DMF (20 mL). The resulting reaction mixture was heated to 95° C. and stirred for 3 hours. The reaction was the quenched with saturated aqueous 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=359 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with saturated aqueous 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-0015b6ef997643ae8148ce173bb10ace
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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