Potassium Carbonate → HCID 178452618, compound

HRID 1040464Notes

Reaction equation

HRID 1040464 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1([C:11](=[NH:13])[NH2:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23](=O)[C:24]([F:27])([F:26])[F:25]>CC#N.CCOC(C)=O>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1([C:11]2[NH:12][CH:22]=[C:23]([C:24]([F:27])([F:26])[F:25])[N:13]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 58430989tert-butyl N-(1-carbamimidoylcyclopropyl)carbamate

Product 1

HCID 178452618HCID 178452618, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of (1-Carbamimidoyl-cyclopropyl)-carbamic acid tert-butyl ester (488 mg, 2.45 mmol) and K2CO3 (676 mg, 4.90 mmol) in MeCN (14 mL) at 85° C. was added a solution of 3-Bromo-1,1,1-trifluoro-propan-2-one (400 mg, 2.09 mmol) in MeCN (10 mL) drop wise over 30 min. The dilute reaction mixture (0.1 N) was stirred at 85° C. for 3 h before cooled to room temperature. Diluted with EtOAc and extracted three times, washed with water and Brine. Dried over MgSO4, filtered and concentrated down in vacuo. The mixture was purified by reverse phase preparation HPLC to give 32 mg of [1-(4-Trifluoromethyl-1H-imidazol-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester as a yellow solid, m/z 292.42 [M+1]+

Workup

  1. temperaturebefore cooled to room temperature
  2. extractionextracted three times
  3. washwashed with water and Brine
  4. dry with materialDried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down in vacuo
  7. customThe mixture was purified by reverse phase preparation HPLC

Sources & evidence

ORD record
ord-c0d64840e62c4b659d072e7a0b64086a
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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