Hydrochloric Acid → HCID 86601931, compound

HRID 1784307Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:15]([CH2:16][CH2:17][CH:18]3OCC[O:19]3)[C:14]3[CH:23]=[C:24]([C:27]([N:29]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH:25]=[CH:26][C:13]=3[N:12]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl>O1CCCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:15]([CH2:16][CH2:17][CH:18]=[O:19])[C:14]3[CH:23]=[C:24]([C:27]([N:29]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])=[O:28])[CH:25]=[CH:26][C:13]=3[N:12]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 2-[(4-acetylphenyl)amino]-1-[2-(1,3-dioxolan-2-yl)ethyl]-N,N-bis(3-methylbutyl)-1H-benzimidazole-6-carboxamide (900 mg) in a mixture of tetrahydrofuran (30 ml) and aqueous hydrochloric acid (3N, 40 ml) is stirred for 18 hours at a temperature of approximately 20° C. then concentrated under reduced pressure at 40° C. Dichloromethane (100 ml) is added to the remaining aqueous phase. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of a beige foam (820 mg, 99% yield).

Workup

concentrationthen concentrated under reduced pressure at 40° C
additionDichloromethane (100 ml) is added to the remaining aqueous phase
extractionAfter decantation and extractions
washthe combined organic phases are washed with salt water
dry with materialdried over Na2SO4
concentrationthen concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record: ord-ea252ab4b008481b8b31d7f3cb2bdcdc
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501525B2

Reaction notes

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