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Water → 1-(Pyridin-4-yl)-4-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylamino)piperidine-4-carboxylic acid methyl ester

HRID 412604
Notes
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Reaction equation

HRID 412604 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH2:17])[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].Cl[S:19]([C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][N:28]([C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])[CH2:29]2)=[CH:24][CH:23]=1)(=[O:21])=[O:20].N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([NH:17][S:19]([C:22]2[CH:31]=[C:30]3[C:25]([CH2:26][CH2:27][N:28]([C:32](=[O:37])[C:33]([F:36])([F:34])[F:35])[CH2:29]3)=[CH:24][CH:23]=2)(=[O:20])=[O:21])[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 113453664-Amino-1-(pyridin-4-yl)piperidine-4-carboxylic acid methyl ester

Product 1

HCID 113530021-(Pyridin-4-yl)-4-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylamino)piperidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-amino-1-(pyridin-4-yl)piperidine-4-carboxylic acid methyl ester (330 mg) in chloroform (5 ml) were added 7-chlorosulfonyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (Journal of Medicinal Chemistry, vol. 23, No.8, p. 837 (1980)) (500 mg) and pyridine (0.23 ml), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, water was added, and the mixture was extracted with chloroform and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was dried under reduced pressure to give the title compound (627 mg).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with chloroform
  3. washwashed successively with water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-7f2356ad4cca4239a069d7169d033282
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562828B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes