2-CYCLOPROPYLETHANETHIOAMIDE → HCID 86649532, compound

HRID 1807678Notes

Reaction equation

HRID 1807678 reaction equation
Br[CH:2]1[CH2:14][CH2:13][C:5]2[N:6]=[C:7]([NH:9][C:10](=[O:12])[CH3:11])[S:8][C:4]=2[C:3]1=O.[CH:16]1([CH2:19][C:20]([NH2:22])=[S:21])[CH2:18][CH2:17]1>CO.[OH-].[O-2].[P-3].[Mo]>[CH:16]1([CH2:19][C:20]2[S:21][C:2]3[CH2:14][CH2:13][C:5]4[N:6]=[C:7]([NH:9][C:10](=[O:12])[CH3:11])[S:8][C:4]=4[C:3]=3[N:22]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 221409602-CYCLOPROPYLETHANETHIOAMIDEHCID 57741262N-(6-Bromo-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide

Product 1

HCID 86649532HCID 86649532, compound

Reagents, catalysts & solvents 2

HCID 15935011104-88-4CatalystHCID 887MethanolSolvent

Procedure

N-(6-Bromo-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide (Stage T.3, 347 mg, 1.200 mmol) was dissolved in MeOH (10 mL) and 2-cyclopropyl-thioacetamide (Can. J. Chem 1995 Vol. 73 1468-1477, 166 mg, 1.440 mmol) and ammonium phosphomolybdate (225 mg, 0.120 mmol) were added. The RM was stirred at rt for 20 h then heated at 50° C. for 3 h, 60° C. for 2 h and then refluxed for 24 h. The RM was partitioned between EtOAc/H2O. The organic layer was dried over Na2SO4 and evaporated. The raw material was chromatographied with MPLC C18 H2O 0.1% TFA/CH3CN 0.1% TFA, gradient 0-50%. Product containing fractions were neutralized with NaHCO3, extracted with EtOAc and lyophilized from dioxane to give the title compound as a white solid (M+H=306.2; M−H=304.2; tR 5.12 min (Method F)).

Workup

  1. temperaturethen heated at 50° C. for 3 h, 60° C. for 2 h
  2. temperaturerefluxed for 24 h
  3. customThe RM was partitioned between EtOAc/H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. additionProduct containing fractions
  7. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-257e091b7d1140488a5ceb729278379e
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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