Hydrochloric Acid → HCID 86601373, compound

HRID 346859Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:21][CH:22]=2)[CH:17]=[C:16]1[CH3:34].[CH3:35][N:36]([CH3:40])[C:37](Cl)=[O:38].CCOCC.Cl>N1C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:37](=[O:38])[N:36]([CH3:40])[CH3:35])=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([OH:33])([C:25]([F:26])([F:27])[F:28])[C:29]([F:32])([F:31])[F:30])=[CH:21][CH:22]=2)[CH:17]=[C:16]1[CH3:34]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 25 mg (0.052 mmol) 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-oxazol-2-yl}-phenol (example 99) in 1 mL of pyridine was treated with 28 mg (0.26 mmol) of dimethyl carbamoylchloride and stirred at 60° C. for 2 hours. Et2O and aqueous HCl were added and the phases separated. The aqueous phase was extracted with Et2O and the combined organic phases dried over Na2SO4. Evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 1:1 yielded 19 mg (66%) of dimethyl-carbamic acid 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-oxazol-2-yl}-phenyl ester, light yellow solid, MS: 556 (MH+).

Workup

customthe phases separated
extractionThe aqueous phase was extracted with Et2O
dry with materialthe combined organic phases dried over Na2SO4
customEvaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 1:1

Sources & evidence

ORD record: ord-e7dff9f25d64409a98eb9429f146464e
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173048B2

Reaction notes

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