Hydrochloric Acid → HCID 86714451, compound

HRID 1750243Notes

Reaction equation

HRID 1750243 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[C:17]([F:20])([F:19])[F:18])=[C:6]([NH:21][C:22](=O)[CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH:5]=1.Cl.O>O1CCOCC1>[S:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[CH2:23][C:22]1[N:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[C:17]([F:19])([F:18])[F:20])[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:30])=[CH:5][C:6]=2[N:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 867144503-(2-Thiophen-2-yl-acetylamino)-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester

Product 1

HCID 86714451HCID 86714451, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.75 g 3-(2-Thiophen-2-yl-acetylamino)-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester with 10 ml of 4M hydrochloric acid in dioxane were heated in a microwave reactor to 110° C. for 5 h. 3 ml water was added to the reaction mixture, which was reacted again to 110° C. for 2 h. The mixture was then concentrated in vacuo, the residue taken up in ethyl acetate and water, and the pH of the aqueous phase was brought to 4. The phases were separated, and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, concentrated and 0.75 g (100%) of 2-Thiophen-2-ylmethyl-1-(2-trifluoromethyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid were obtained.

Workup

  1. customwas reacted again to 110° C. for 2 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate twice
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad1e107b884441d3bc2d27af5c41d160
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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