Dimethylformamide → HCID 68870301, compound

HRID 1260974Notes

Reaction equation

HRID 1260974 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:34])[C@@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:25])=O)=[CH:19][CH:18]=3)[CH2:13][C@H:12]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[O:9])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:41][N:42](C=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([CH3:34])[C@@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([NH:42][CH3:41])=[O:25])=[CH:19][CH:18]=3)[CH2:13][C@H:12]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 689390336-[(3R,4R)-4-[(4-Chlorobenzoyl)methylamino]-3-(3,4-dichlorophenyl)-1-piperidinyl]-3-pyridinecarboxylic acid

Product 1

HCID 68870301HCID 68870301, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (0.150 g) obtained in Example 500 in THF (5 mL) were added oxalyl chloride (38 μL) and DMF (3 μL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated, and to a solution of the residue in THF (2 mL) was added a solution of methylamine (0.0269 g) in THF (5 mL), and the mixture was stirred for 10 min. To the reaction mixture was added water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure to give the title compound (0.039 g, 25%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionto a solution of the residue in THF (2 mL) was added a solution of methylamine (0.0269 g) in THF (5 mL)
  3. stirringthe mixture was stirred for 10 min
  4. additionTo the reaction mixture was added water
  5. extractionthe resultant product was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. customdried
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee044acdc3ae40b799ade5625c004deb
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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