2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 70148942, compound

HRID 2230734Notes

Reaction equation

HRID 2230734 reaction equation
[Na].[C:2]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[F:25][C:26]([F:37])([F:36])[CH2:27]OS(C(F)(F)F)(=O)=O>CN(C)C=O>[C:2]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:17]([CH2:27][C:26]([F:37])([F:36])[F:25])[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 5360545SodiumHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 70148942HCID 70148942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Add to a suspension of sodium hydrdide (0.029 g, 1.21 mmol) in anhydrous dimethylformamide (5 mL) a suspension of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan (0.38 g, 1.2 mmol, Preparation 9) in anhydrous dimethylformamide (7 mL). Stir for 3 hours at room temperature and add a large excess of 1,1,1-trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester. Stir overnight at room temperature, quench the reaction with water, wash the organic phase with water, dry (MgSO4), filter and concentrate in vacuo to afford 4-[1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester. Repeat this preparation using 2.88 mmol of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan. Combine the product from both reactions and purify by column chromatography on silica gel eluting with 30% ethyl acetate in hexane and concentrate the appropriate fractions to afford 0.48 g of 4-[1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Workup

  1. stirringStir overnight at room temperature
  2. customquench
  3. customthe reaction with water
  4. washwash the organic phase with water
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-da9aaa5646804a84abc6626f90d6414f
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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