Pyridine → HCID 58786412, compound

HRID 1376044Notes

Reaction equation

HRID 1376044 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 587864641,1-Dimethylethyl 4-[2-amino-1-(2-fluorophenyl)ethyl]-1-piperazinecarboxylate

Product 1

HCID 58786412HCID 58786412, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[2-Amino-1-(2-fluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (207) (1.45 g, 4.48 mmol) in MeCl2 (10 mL) was added methanesulfonyl chloride (0.51 g, 4.48 mmol) and pyridine. The reaction was allowed to stir at room temperature for 18 h. The reaction mixture was then diluted with EtOAc (50 mL) and washed with H2O (50 mL) and brine (50 mL). The organic phase was concentrated to dryness yielding 1.43 g (80%) product.

Workup

  1. washwashed with H2O (50 mL) and brine (50 mL)
  2. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-86015d8115f241f48e3cabb3ed0e65cf
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…