Hydrochloric Acid → HCID 86714428, compound

HRID 1750219Notes

Reaction equation

HRID 1750219 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:6]([NH:18][C:19](=O)[CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:19]([CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[N:18][C:6]=2[CH:5]=1)=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86714427HCID 86714427, compound

Product 1

HCID 86714428HCID 86714428, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

20.0 g 4-(Cyclohexylmethyl-amino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester were dissolved in 65 ml dioxane and reacted with 33 ml of 4M hydrochloric acid in dioxane at rt for 4 h. The reaction was concentrated and the residue purified by chromatography (silica, ethyl acetate/heptane) to yield 13.6 g (71%) of 1-Cyclohexylmethyl-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue purified by chromatography (silica, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-21582fcf8b8549038c6221cf991fd180
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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