Pyridine → HCID 10203128, compound

HRID 1935238Notes

Reaction equation

HRID 1935238 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[CH:28]1([S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH:42]([CH2:46][CH:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)[C:43](O)=[O:44])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:52][C:53]1[S:54][CH:55]=[CH:56][N:57]=1.N1C=CC=CC=1>C(Cl)Cl.O>[CH:28]1([S:33]([C:36]2[CH:37]=[CH:38][C:39]([CH:42]([CH2:46][CH:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)[C:43]([NH:52][C:53]3[S:54][CH:55]=[CH:56][N:57]=3)=[O:44])=[CH:40][CH:41]=2)(=[O:35])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 5

HCID 1049PyridineHCID 21552-AminothiazoleHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 22467920HCID 22467920, compound

Product 1

HCID 10203128HCID 10203128, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of triphenylphosphine (106 mg, 0.40 mmol) and N-bromosuccinimide (82 mg, 0.45 mmol) in methylene chloride (1.35 mL) was cooled to 0° C. and then treated with a solution of 2-(4-cyclopentanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (94.8 mg, 0.27 mmol) in methylene chloride. The reaction mixture was stirred at 25° C. for 45 min. At this time, the reaction was treated with 2-aminothiazole (35 mg, 0.35 mmol) and pyridine (0.03 ml, 0.40 mmol). The reaction was stirred at 25° C. for 18 h. The reaction was then diluted with water (100 mL) and extracted with chloroform (3×50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(4-cyclopentanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (84 mg, 71.8%) as a light-orange solid: mp 180-182° C.; EI-HRMS m/e calcd for C22H28N2O3S2 (M+) 432.1541 found 432.1543.

Workup

  1. stirringThe reaction was stirred at 25° C. for 18 h
  2. extractionextracted with chloroform (3×50 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48760f30327a4b20832c973bc7b2a45f
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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