Hydrochloric Acid → HCID 58156074, compound

HRID 538174Notes

Reaction equation

HRID 538174 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]=[CH:23][C:24]([F:27])=[C:25]([CH3:26])[C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.Cl>C(O)(=O)C>[F:27][C:24]1[CH:23]=[CH:22][C:14]2[NH:15][C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[N:12][C:13]=2[C:25]=1[CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66937418HCID 66937418, compound

Product 1

HCID 58156074HCID 58156074, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[5-fluoro-1-(2-methoxy-ethoxymethyl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.131 g, 0.481 mmol), glacial acetic acid (4.8 mL), and 6M aqueous HCl (4.8 mL) was heated at 100° C. for 4 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 (75.0 mg, 60%). MS (ESI/CI): mass calcd. for C12H9FN4O2, 260.1; m/z found, 261.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.88 (s, 1H), 8.29 (s, 1H), 7.35 (dd, J=8.7, 4.5 Hz, 1H), 7.06 (dd, J=10.4, 8.8 Hz, 1H), 2.46 (d, J=1.3 Hz, 3H).

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-c26ee05794d8490d8061bce7ab499351
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

Loading…