HCID 68405926, compound → HCID 86606573, compound

HRID 2244444Notes

Reaction equation

HRID 2244444 reaction equation
C1(COC(=O)[N:7]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14](=[O:23])[NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[N:17]=2)CC1>FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>[CH3:22][C:18]1[N:17]=[C:16]([NH:15][C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[NH:7][CH2:24][CH:25]2[CH2:27][CH2:26]2)=[O:23])[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 1

HCID 68405926HCID 68405926, compound

Product 1

HCID 86606573HCID 86606573, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

Cyclopropylmethyl-[2-methyl-4-(2-methyl-pyrimidin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid cyclopropylmethyl ester (example 205, 0.091 g, 0.227 mmol) was dissolved in 1 mL trifluoroacetic acid and stirred at 50° C. for 3 h. The reaction mixture was diluted with 20 mL saturated sodium bicarbonate solution and extracted three times with ethyl acetate (30 mL each). The organic phases were pooled, dried with sodium sulfate and evaporated. The crude product was flash-chromatographed on silica gel with heptane/ethyl acetate 100:0→0:100 gradient to yield the desired compound as a white solid (37 mg, 54%), MS (ISP): m/e=304.0 (M+H+).

Workup

  1. extractionextracted three times with ethyl acetate (30 mL each)
  2. dry with materialdried with sodium sulfate
  3. customevaporated
  4. customThe crude product was flash-chromatographed on silica gel with heptane/ethyl acetate 100:0→0:100 gradient

Sources & evidence

ORD record
ord-3a35859ba11d4da5ab0b1dc69816fa64
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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