2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride → 1-(Pyridin-4-yl)-4-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylaminomethyl)piperidine-4-carboxylic acid ethyl ester

HRID 412608Notes

Reaction equation

HRID 412608 reaction equation
Br.Br.[CH2:3]([O:5][C:6]([C:8]1([CH2:20][NH2:21])[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4].Cl[S:23]([C:26]1[CH:35]=[C:34]2[C:29]([CH2:30][CH2:31][N:32]([C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])[CH2:33]2)=[CH:28][CH:27]=1)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH2:3]([O:5][C:6]([C:8]1([CH2:20][NH:21][S:23]([C:26]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][N:32]([C:36](=[O:41])[C:37]([F:40])([F:38])[F:39])[CH2:33]3)=[CH:28][CH:27]=2)(=[O:24])=[O:25])[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 696973274-Aminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrobromide

Product 1

HCID 865907251-(Pyridin-4-yl)-4-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylaminomethyl)piperidine-4-carboxylic acid ethyl esterYield 48.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-aminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrobromide (423 mg) were added pyridine (2 ml) and 7-chlorosulfonyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (273 mg), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated and water was added. The mixture was extracted with chloroform and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=4:1) and dried under reduced pressure to give the title compound (222 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionwater was added
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=4:1)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-edc995e474914abeab1f7dda054d6543
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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