Dimethylformamide → HCID 56961708, compound

HRID 1748628Notes

Reaction equation

HRID 1748628 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7][N:8]([CH3:11])C=O.[F:12][C:13]1[C:14]([N:23]2[C:27]([CH3:28])=[C:26]([C:29]([OH:31])=O)[CH:25]=[N:24]2)=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1>ClCCl>[F:12][C:13]1[C:14]([N:23]2[C:27]([CH3:28])=[C:26]([C:29]([NH:15][C:14]3[CH:7]=[N:8][C:11]([C:26]4[CH2:25][CH2:2][CH:1]([OH:5])[CH2:28][CH:27]=4)=[C:18]([CH3:17])[CH:13]=3)=[O:31])[CH:25]=[N:24]2)=[N:15][CH:16]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86692504HCID 86692504, compound

Product 1

HCID 56961708HCID 56961708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.14 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 1-(3-fluoro-5-trifluoromethylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid (120 mg) described in Reference Example 130 in dichloromethane (5 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated, and toluene (5 ml) was added to the resulted reaction mixture. Next, a solution of 2-(4-hydroxycyclohex-1-en-1-yl)-3-methyl-5-aminopyridine (81 mg) described in Reference Example 111 in pyridine (5 ml) was added thereto and stirred at room temperature overnight. After the reaction, 1N aqueous solution of sodium hydroxide was added under ice-cooling and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with a silica gel column chromatography (chloroform/methanol), washed with ethanol and the resulting solid was collected by filtration and dried at 60° C. in vacuo to give the titled compound (107 mg) as a white solid.

Workup

  1. customThe solvent and an excess amount of oxalyl chloride were evaporated
  2. additiontoluene (5 ml) was added to the resulted reaction mixture
  3. additionwas added
  4. stirringstirred at room temperature overnight
  5. customAfter the reaction, 1N aqueous solution of sodium hydroxide
  6. additionwas added under ice-
  7. temperaturecooling
  8. extractionextracted with chloroform
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe resulting residue was purified with a silica gel column chromatography (chloroform/methanol)
  12. washwashed with ethanol
  13. filtrationthe resulting solid was collected by filtration
  14. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-1010fcd7a9474a6db1020f3ec4384c44
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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