Trifluoroacetic acid → HCID 58932988, compound

HRID 1486772Notes

Reaction equation

HRID 1486772 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([C:18]2[C:26]3[N:25]=[C:24]([CH:27]([CH3:29])[CH3:28])[NH:23][C:22]=3[CH:21]=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([C:18]2[C:26]3[N:25]=[C:24]([CH:27]([CH3:29])[CH3:28])[NH:23][C:22]=3[CH:21]=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66810963HCID 66810963, compound

Product 1

HCID 58932988HCID 58932988, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[(2-isopropyl-1H-benzoimidazole-4-carbonyl)amino]methyl}-piperidine-1-carboxylic acid tert-butyl ester (10.8 g, 27.0 mmol) dissolved in dichloromethane (50 mL) at 0° C. was slowly added trifluoroacetic acid (50 mL) in 5 mL portions. The solution was allowed to warm to room temperature, stirred for an additional 20 minutes then evaporated in vacuo. Excess trifluoroacetic acid was removed by co-evaporation with toluene. The residue was then dissolved in a minimal volume of dichloromethane and slowly added to diethyl ether (1 L) at 0° C. The resulting slurry was stirred for 2 h at room temperature then filtered to afford the bis-trifluoroacetate salt of the title compound as a light brown solid (12.7 g, 24.0 mmol, 89%). (m/z): [M+H]+ calcd for C12H24N4O, 301.21. found 301.5. Retention time (anal. HPLC: 2-50% MeCN/H2O over 6 min)=1.65 min. 1H NMR (300 MHz, MeOD-d3): δ (ppm) 1.59 (d, 6H), 1.60 (m, 1H), 2.03 (m, 2H), 2.04 (m, 1H), 3.00 (m, 2H), 3.43 (m, 2H), 3.45 (m, 2H), 3.63 (septet, 1H), 7.63 (t, 1H), 7.90 (d, 1H), 7.96 (d, 1H), 9.04 (t, 1H).

Workup

  1. customthen evaporated in vacuo
  2. customExcess trifluoroacetic acid was removed by co-evaporation with toluene
  3. dissolutionThe residue was then dissolved in a minimal volume of dichloromethane
  4. additionslowly added to diethyl ether (1 L) at 0° C
  5. stirringThe resulting slurry was stirred for 2 h at room temperature
  6. filtrationthen filtered

Sources & evidence

ORD record
ord-80bb2006ab874d0e9053b440d702d626
Source dataset
uspto-grants-2016_08
Patent number
US09428489B2

Reaction notes

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