2-Aminothiazole → HCID 10110484, compound

HRID 397187Notes

Reaction equation

HRID 397187 reaction equation
[CH:1]1([O:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]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.[NH2:54][C:55]1[S:56][CH:57]=[CH:58][N:59]=1>ClCCl.O>[CH:1]1([O:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:9]([NH:54][C:55]2[S:56][CH:57]=[CH:58][N:59]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12044176HCID 12044176, compound

Product 1

HCID 10110484HCID 10110484, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of rac-(cyclohex-2-enyloxy)-(3,4-dichloro-phenyl)-acetic acid (89 mg, 0.28 mmol) in dichloromethane (10 mL) was treated with BOP reagent (187 mg, 0.42 mmol), triethylamine (0.12 mL, 0.85 mmol), and 2-aminothiazole (42 mg, 0.42 mmol) at 25° C. The resulting brownish-orange solution was then stirred 16 h at 25° C., then was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide solution (1×10 mL), 1N hydrochloric acid (1×10 mL), and brine (1×10 mL), then were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate) to provide rac-(cyclohex-2-enyloxy)-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (99 mg, 92% yield) as a white foam: EI-HRMS m/e calcd for C17H16Cl2O2N2S (M+) 382.0309, found 382.0308.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe combined organic layers were washed with water (1×10 mL), 1N sodium hydroxide solution (1×10 mL), 1N hydrochloric acid (1×10 mL), and brine (1×10 mL)
  3. dry with materialwere dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-92f4fc712535490ba833e7945db3da21
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

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