Pyridine → HCID 22315127, compound

HRID 1355151Notes

Reaction equation

HRID 1355151 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[CH2:28]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH:41]([CH2:45][CH:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)[C:42]([OH:44])=O)=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:29][CH2:30][CH3:31].[NH2:51][C:52]1[S:53][CH:54]=[CH:55][N:56]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:28]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH:41]([CH2:45][CH:46]2[CH2:47][CH2:48][CH2:49][CH2:50]2)[C:42]([NH:51][C:52]2[S:53][CH:54]=[CH:55][N:56]=2)=[O:44])=[CH:37][CH:36]=1)(=[O:33])=[O:34])[CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 5

HCID 1049PyridineHCID 21552-AminothiazoleHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 22315148HCID 22315148, compound

Product 1

HCID 22315127HCID 22315127, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of triphenylphosphine (99 mg, 0.37 mmol) and N-bromosuccinimide (76 mg, 0.42 mmol) in methylene chloride (1.26 mL) cooled to 0° C. was treated with 2-[4-(butane-1-sulfonyl)-phenyl]-3-cyclopentyl-propionic acid (85 mg, 0.25 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 (33 mg, 0.32 mmol) and pyridine (0.03 mL, 0.37 mmol). The reaction was stirred at 25° C. for 18 h. The reaction mixture was then concentrated in vacuo to remove methylene chloride. At this time, the reaction was diluted with water (50 mL) and extracted with chloroform (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50/50 hexanes/ethyl acetate) afforded 2-[4-(butane-1-sulfonyl)-phenyl]-3-cyclopentyl-N-thiazol-2-yl-propionamide (69.3 mg, 65.6%) as an off-white solid: mp 163–165° C.; EI-HRMS m/e calcd for C21H28N2O3S2 (M+) 420.1541 found 420.1535.

Workup

  1. stirringThe reaction was stirred at 25° C. for 18 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customto remove methylene chloride
  4. additionAt this time, the reaction was diluted with water (50 mL)
  5. extractionextracted with chloroform (3×50 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6c5901e7acb4726bc2b9574eebaf2d9
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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