Acetate-hydrochloric acid → HCID 178475080, compound

HRID 1630261Notes

Reaction equation

HRID 1630261 reaction equation
Cl.[C:2]([OH:5])(=O)[CH3:3].[CH2:6]([O:13][CH2:14][C@@H:15]([C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:25][C:19]=2[N:18]=1)[NH2:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:6]([O:13][CH2:14][C@H:15]([NH:16][C:2](=[O:5])[CH3:3])[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[CH:25][C:19]=2[N:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 22641269Acetate-hydrochloric acidHCID 178511835HCID 178511835, compound

Product 1

HCID 178475080HCID 178475080, compoundYield 32%

Procedure

Proceeding as in Example 1, but substituting acetic acid hydrochloride and (R)-2-(benzyloxy)-1-(5-(4-fluorophenoxy)-1H-benzo[d]imidazol-2-yl)ethanamine, gave Compound 60, (R)—N-(2-(benzyloxy)-1-(5-(4-fluorophenoxy)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide (22 mg, 32%). 1H-NMR (400 MHz, CDCl3): σ 7.50 (d, 1H), 7.38-7.30 (m, 5H), 7.13 (br s, 1H), 7.03-6.93 (m, 5H), 6.71 (d, 1H), 5.33 (q, 1H), 4.68-4.58 (m, 2H), 4.19 (dd, 1H), 3.86 (dd, 1H), 2.06 (s, 3H). MS (EI) for C24H22FN3O3. found 420.2 (MH+).

Sources & evidence

ORD record
ord-03f323f05f7e4454807edae260f480b0
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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