Dimethylformamide → HCID 11755068, compound

HRID 719864Notes

Reaction equation

HRID 719864 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:28])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:19]([Cl:27])[CH:18]=2)[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1.[SH:29][CH:30](O)C.CN(C)[CH:35]=[O:36]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:27][C:19]1[CH:18]=[C:17]([C@@H:10]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]([NH:8][C:5]2[CH:4]=[N:3][C:2]([S:29][CH2:30][CH2:35][OH:36])=[CH:7][N:6]=2)=[O:28])[CH:22]=[CH:21][C:20]=1[S:23]([CH3:26])(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 4713212Mercapto-ethanolHCID 86593779N-(5-bromo-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide

Product 1

HCID 11755068HCID 11755068, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the N-(5-bromo-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (94 mg, 0.19 mmol), mercaptoethanol (0.031 mL, 0.44 mmol), and tetrakis(triphenylphosphine)palladium(0) (111 mg, 0.097 mmol) in anhydrous N,N-dimethylformamide (0.5 mL) was heated at 120° C. in a sealed tube. After 3 h, the mixture was allowed to cool to 25° C., diluted with water, and then extracted with diethyl ether. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck silica gel 60, 230–400 mesh, 55% ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylsulfanyl)-pyrazin-2-yl]-propionamide (58 mg, 62%) as a light brown foam: mp=78–81° C.; (ES)+-HRMS m/e calcd for C21H27ClN3O4S2 (M+H)+ 484.1126, found 484.1131.

Workup

  1. temperatureto cool to 25° C.
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9bcfcdd4d8404d18a441cfb81bae144d
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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