Hydrochloric Acid → HCID 86714424, compound

HRID 1750213Notes

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][N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)[CH:5]=1.Cl.[OH-].[Na+]>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][N:19]1[CH:23]=[CH:22][CH:21]=[N:20]1)[CH2:14][CH3:15])[CH3:13]

Participants

Conditions

Temperature: 110 °C

Procedure

To 2.28 g 4-(1-Ethyl-propylamino)-3-(2-pyrazol-1-yl-acetylamino)-benzoic acid methyl ester were added 50 ml of 4M hydrochloric acid in dioxane. Divided into five portions the reaction mixture was heated to 110° C. for 15 min in a microwave reactor. After cooling to the reaction mixture 6 ml of 10 M aqueous sodium hydroxide solution were added slowly. After 30 min at rt the reaction mixture was concentrated to a third of its volume and adjusted to pH 4 by the addition of 2M aqueous hydrochloric acid. It was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. 1.86 g (90%) of 1-(1-Ethyl-propyl)-2-pyrazol-1-ylmethyl-1H-benzoimidazole-5-carboxylic acid were obtained.

Workup

additionwere added slowly
concentrationAfter 30 min at rt the reaction mixture was concentrated to a third of its volume
additionadjusted to pH 4 by the addition of 2M aqueous hydrochloric acid
extractionIt was extracted with ethyl acetate three times
dry with materialThe combined organic phases were dried over sodium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-30ef379bab3a49799918bb2d9372776d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156796B2

Reaction notes

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