Hydrochloric Acid → 1-(1-Ethyl-propyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid

HRID 1750211Notes

Reaction equation

HRID 1750211 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:6]([NH:16][C:17](=O)[CH2:18][C:19]2[S:23][CH:22]=[N:21][CH:20]=2)[CH:5]=1.Cl.O>O1CCOCC1>[CH2:12]([CH:11]([N:10]1[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:25])=[CH:5][C:6]=2[N:16]=[C:17]1[CH2:18][C:19]1[S:23][CH:22]=[N:21][CH:20]=1)[CH2:14][CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86714421HCID 86714421, compound

Product 1

HCID 867144221-(1-Ethyl-propyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To 2.16 g of 4-(1-Ethyl-propylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester were added 15 ml of 4M hydrochloric acid in dioxane. The reaction was divided in three portions and each was heated at 130° C. in a microwave reactor for 15 min. 2 ml of water were added to each vial and the reaction mixtures were heated to 140° C. for 15 min. The combined reaction mixtures were concentrated and the residue purified by chromatography (silica, ethyl acetate/heptane) to yield 1.50 g (77%) of 1-(1-Ethyl-propyl)-2-thiazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid.

Workup

  1. customthe reaction mixtures
  2. temperaturewere heated to 140° C. for 15 min
  3. customThe combined reaction mixtures
  4. concentrationwere concentrated
  5. customthe residue purified by chromatography (silica, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-c616ecd207d345b7a3e73c6b0f4baf47
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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