Ammonia → HCID 23114826, compound

HRID 2080420Notes

Reaction equation

HRID 2080420 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:12]2[N:17]=[CH:16][C:15]([C:18](O)=O)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=[O:30].[NH3:33].[ClH:34]>CN(C)C=O.ClCCl>[Cl:34][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH2:17])=[O:30])=[CH:18][N:33]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 23114724[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid

Product 1

HCID 23114826HCID 23114826, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (4 ml) suspension of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (100 mg, 0.236 mmol) obtained in Example 50 were added thionyl chloride (1.00 ml) and N,N-dimethylformamide (one drop). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated to dryness. The residue thus obtained was dissolved in dichloromethane (6 ml). A 28% aqueous ammonia (2 ml) was added to the resulting solution. After the mixture was stirred at room temperature for 3 hours, the reaction mixture was acidified with 1N hydrochloric acid. The resulting mixture was concentrated and the solid thus formed was collected by filtration. The solid thus obtained was washed with water and ethanol and then, recrystallized from ethanol to give the title compound (47.9 mg, 0.113 mmol, 46%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe residue thus obtained
  3. stirringAfter the mixture was stirred at room temperature for 3 hours
  4. concentrationThe resulting mixture was concentrated
  5. customthe solid thus formed
  6. filtrationwas collected by filtration
  7. customThe solid thus obtained
  8. washwas washed with water and ethanol
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d6031eca611a440395a32fbe0686c4ac
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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