Hydrochloric Acid → HCID 178524817, compound

HRID 408745Notes

Reaction equation

HRID 408745 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:15](COCCOC)[C:14]3[CH:22]=[C:23]([O:32][C:33]([F:36])([F:35])[F:34])[C:24]([N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:25][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.Cl>C(O)(=O)C>[N:26]1([C:24]2[C:23]([O:32][C:33]([F:34])([F:36])[F:35])=[CH:22][C:14]3[NH:15][C:11]([N:9]4[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]4)=[N:12][C:13]=3[CH:25]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66937281HCID 66937281, compound

Product 1

HCID 178524817HCID 178524817, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[1-(2-methoxy-ethoxymethyl)-5-piperidin-1-yl-6-trifluoromethoxy-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.300 g, 0.586 mmol), glacial acetic acid (5.9 mL), and 6M aqueous HCl (6.9 mL) was heated at 100° C. for 4.5 h in a sealed tube. The reaction mixture was cooled to 23° C. and then 0° C. The resulting precipitate was filtered and washed with cold water to yield the titled compound (60.0 mg, 26%). MS (ESI/CI): mass calcd. for C17H16F3N6O3, 395.1; m/z found, 396.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.84 (d, J=0.6 Hz, 1H), 8.27 (d, J=0.6 Hz, 1H), 7.47 (br s, 1H), 7.21 (br s, 1H), 2.98-2.89 (m, 4H), 1.71-1.59 (m, 4H), 1.58-1.47 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. custom0° C
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with cold water

Sources & evidence

ORD record
ord-c724ac3ff85f48639b03b39cf3e066e7
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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