Hydrochloric Acid → HCID 135887206, compound

HRID 1627227Notes

Reaction equation

[C:1]([C:3]1[CH:41]=[CH:40][C:6]([CH2:7][NH:8][C:9]([C:11]2[N:12](COCC[Si](C)(C)C)[C:13]([CH3:31])=[C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([C:25]3[O:29][N:28]=[C:27]([CH3:30])[N:26]=3)=[CH:19]4)[N:15]=2)=[O:10])=[CH:5][CH:4]=1)#[N:2].Cl>O1CCOCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]([C:11]2[NH:12][C:13]([CH3:31])=[C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([C:25]3[O:29][N:28]=[C:27]([CH3:30])[N:26]=3)=[CH:19]4)[N:15]=2)=[O:10])=[CH:40][CH:41]=1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-Methyl-4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indol-5-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid 4-cyano-benzylamide (75 mg, 0.13 mmol) in of dioxane (2.5 ml) is added aqueous HCl (3M, 2.5 ml) and is the mixture is heated at 100° C. for 4 hours. The solvent is evaporated and the residue is purified on silica with ethyl acetate/hexane as the eluent to give product 12 mg, 21%, LC/MS ESI m/z (M+H)+=438.4.

Workup

customThe solvent is evaporated
customthe residue is purified on silica with ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-29c56d2b4d6b42ea8c4a29490db0516b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785489B2

Reaction notes

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