Dichloromethane → HCID 86742082, compound

HRID 648506Notes

Reaction equation

HRID 648506 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](C1CCNCC1)=[O:34].C([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C.[CH2:48](Cl)Cl>>[N:43]1[CH:44]=[CH:45][CH:48]=[CH:47][C:46]=1[CH:29]1[CH2:30][CH2:31][CH2:32][N:27]([C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([NH:14][C:8]3[C:7]4[C:12](=[CH:13][C:4]([C:3]([F:25])([F:24])[F:2])=[CH:5][CH:6]=4)[N:11]=[CH:10][CH:9]=3)=[CH:16][CH:17]=2)[C:28]1=[S:33]=[O:34]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13603946HCID 13603946, compoundHCID 13825050HCID 13825050, compound

Product 1

HCID 86742082HCID 86742082, compound

Procedure

4-[[7-(Trifluoromethyl)-4-quinolyl]amino]benzoyl chloride hydrochloride (0.69 g) was added slowly to a stirred mixture of 4-[(2-pyridyl)sulfinyl]piperidine hydrochloride (0.50 g) and triethylamine (1.72 ml) in dry methylene chloride (22 ml) at room temperature. The resultant mixture was stirred at the same temperature for 1.5 hours and concentrated in vacuo. The residue was partitioned between chloroform and water. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated to dryness in vacuo. The resultant crystalline residue was recrystallized from a mixture of methylene chloride and methanol and washed successively with methanol and methylene chloride to give 4-[(2-pyridyl(sulfinyl]-1-[4-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperidine (0.59 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between chloroform and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe resultant crystalline residue was recrystallized from a mixture of methylene chloride and methanol
  7. washwashed successively with methanol and methylene chloride

Sources & evidence

ORD record
ord-c67dc822dd1943519f0bae8251ebd547
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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