Hydrochloric Acid → HCID 178442453, compound

HRID 216384Notes

Reaction equation

HRID 216384 reaction equation
Cl.[CH3:2][C:3]([CH3:50])([CH2:48][CH3:49])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][CH:30]([NH:44][C:45](=[O:47])[CH3:46])[C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][N:38]=3)=[CH:33][CH:32]=2)[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1>O1CCOCC1.CO>[CH3:2][C:3]([CH3:50])([CH2:48][CH3:49])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][CH:30]([NH:44][C:45](=[O:47])[CH3:46])[C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][N:38]=3)=[CH:35][CH:36]=2)[NH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68667957N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]-ethyl}acetamide

Product 1

HCID 178442453HCID 178442453, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Hydrogen chloride (4N, 2 mL) in dioxane was added to a solution of N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]-ethyl}acetamide in methanol (4 mL) at ambient temperature. The solution was stirred at 50° C. for 2 hr. Concentration of the solution afforded the title compound as a white solid. 1H NMR (500 MHz, CD3OD) δ 8.95-8.92 (m, 1H), 8.45-8.39 (m, 1H), 8.33 (dd, J=4.5, 9.0 Hz, 1H), 7.97 (d, J=8.5 Hz, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.18 (s, 1H), 5.49 (t, J=8.0 Hz, 1H), 3.56-3.48 (m, 3H), 2.52 (s, 2H), 1.96 (s, 3H), 1.25 (q, J=7.5, 15.0 Hz, 2H), 0.87 (t, J=7.5 Hz, 3H), 0.84 (s, 3H), 0.83 (s, 3H).

Sources & evidence

ORD record
ord-934f91b3a11e49fcb934a9e3dec4343d
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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