Triethylamine → HCID 20144930, compound

HRID 648498Notes

Reaction equation

HRID 648498 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:21])=[O:20])=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.Cl.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:36])=[O:35].C(N(CC)CC)C>C(Cl)Cl>[ClH:21].[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([CH:37]1[CH2:42][CH2:41][N:40]([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)[CH2:39][CH2:38]1)(=[O:35])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13603946HCID 13603946, compoundHCID 13825033HCID 13825033, compound

Product 1

HCID 20144930HCID 20144930, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(B 5) 4-[[7-(Trifluoromethyl)-4-quinolyl]amino]benzoyl chloride hydrochloride (65.20 g) was added slowly to a stirred mixture of 4-[(2-fluorophenyl)sulfonyl]piperidine hydrochloride (47.0 g) and triethylamine (117.2 ml) in dry methylene chloride (1.01 l) at room temperature. The resultant mixture was stirred at the same temperature for 1 hour and under ice cooling for 0.5 hours. The precipitated powder was collected by filtration, washed with a mixture of methylene chloride and water, and suspended in a mixture of chloroform and methanol. Excess methanolic hydrochloric acid was added to the suspension and the resulting solution was concentrated in vacuo to give an oil. The oil was triturated in a mixture of ethyl acetate and ethanol to give powdery 4-[(2-fluorophenyl)sulfonyl]-1-[4-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperidine hydrochloride (46.73 g).

Workup

  1. filtrationThe precipitated powder was collected by filtration
  2. washwashed with a mixture of methylene chloride and water
  3. additionsuspended in a mixture of chloroform and methanol
  4. additionExcess methanolic hydrochloric acid was added to the suspension
  5. concentrationthe resulting solution was concentrated in vacuo
  6. customto give an oil
  7. customThe oil was triturated in a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-68169c71ecec4d48bc306bf092c37756
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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