Hydrochloric Acid → HCID 178444965, compound

HRID 2355300Notes

Reaction equation

Cl.[CH3:2][C:3]([CH3:55])([CH3:54])[CH2:4][C:5]([C:7]1[CH:48]=[CH:47][C:10]([O:11][CH2:12][C:13]2[CH:46]=[CH:45][C:16]([CH2:17][NH:18][C:19]([C:21]3[N:22]=[CH:23][N:24](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:25]=3)=[O:20])=[CH:15][CH:14]=2)=[C:9]([C:49]([F:52])([F:51])[F:50])[C:8]=1[OH:53])=[O:6]>C(O)C>[CH3:2][C:3]([CH3:55])([CH3:54])[CH2:4][C:5]([C:7]1[CH:48]=[CH:47][C:10]([O:11][CH2:12][C:13]2[CH:46]=[CH:45][C:16]([CH2:17][NH:18][C:19]([C:21]3[N:22]=[CH:23][NH:24][CH:25]=3)=[O:20])=[CH:15][CH:14]=2)=[C:9]([C:49]([F:52])([F:51])[F:50])[C:8]=1[OH:53])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

Add a 2.5N solution of hydrogen chloride (10 mL, 25.00 mmol) to 1-trityl-1H-imidazole-4-carboxylic acid 4-[4-(3,3-dimethyl-butyryl)-3-hydroxy-2-trifluoromethyl-phenoxymethyl]-benzylamide (217 mg, 296 μmol) in ethanol (10 mL). Stir the reaction mixture for 1.5 hr at 60° C. Cool the reaction mixture to room temperature and filter the precipitate. To the filtrate add water to precipitate the product. Filter the precipitate and triturate it with ether to remove the remaining trityl impurity. Filter the solid to give the title compound as a white solid (121 mg, 83% yield). MS (m/z): 490 (M+1).

Workup

temperatureCool the reaction mixture to room temperature
filtrationfilter the precipitate
additionTo the filtrate add water
customto precipitate the product
filtrationFilter the precipitate
customtriturate it with ether
customto remove the remaining trityl impurity
filtrationFilter the solid

Sources & evidence

ORD record: ord-312bfafd136240a8862ca236eacd48ac
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754742B2

Reaction notes

Loading…