2-Aminothiazole → Rac-2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxy-n-thiazol-2-yl-acetamide

HRID 1019210Notes

Reaction equation

HRID 1019210 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([NH:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18172604Rac-(3-chloro-4-methanesulfonyl-phenyl)-cyclopentyloxy-acetic acid

Product 1

HCID 10201902Rac-2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxy-n-thiazol-2-yl-acetamideYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of rac-(3-chloro-4-methanesulfonyl-phenyl)-cyclopentyloxy-acetic acid (50 mg, 0.15 mmol) in dichloromethane (10 mL) at 25° C. was added 2-aminothiazole (23 mg, 0.23 mmol), BOP reagent (100 mg, 0.23 mmol) and triethylamine (0.06 mL, 0.45 mmol). The mixture was stirred at 25° C. for 16 h, then it was diluted with water (10 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1N hydrochloric acid (1×10 mL) and brine ( 1×10 mL), then were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (Biotage Flash 40S column, 60/40 hexanes/ethyl acetate) to give rac-2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxy-N-thiazol-2-yl-acetamide(44 mg, 71% yield) as a white solid: EI-HRMS m/e calculated for C17H19N2O4S2Cl (M+) 414.0475, found 414.0481.

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide (1×10 mL), 1N hydrochloric acid (1×10 mL) and brine ( 1×10 mL)
  3. dry with materialwere dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by chromatography (Biotage Flash 40S column, 60/40 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ed834de718834c7583aad483de546e95
Source dataset
uspto-grants-2002_11
Patent number
US06486184B2

Reaction notes

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