Hydrochloric Acid → HCID 178494487, compound

HRID 2247156Notes

Reaction equation

[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]([NH2:20])=[O:19])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.Cl.[CH:28](Cl)(Cl)Cl>>[CH3:28][O:1][CH:2]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]([NH2:20])=[O:19])=[CH:17][C:11]=3[N:10]=2)=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 6212Chloroform

HCID 178513580HCID 178513580, compound

Product 1

HCID 178494487HCID 178494487, compoundYield 47%

Procedure

To a solution of 2-[4-(hydroxy-phenyl-methyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (Example 19, 8.7 mg, 0.02 mmol) in chloroform (1.0 mL) was added concentrated HCl (0.1 mL). The reaction mixture was stirred at RT for 2 h. Organics were removed under reduced pressure, and purification using preparative TLC (silica, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 4.2 mg (47%) of the title compound. HPLC (Method A): Rt=6.97. MS (ESI+): mass calculated for C22H19N3O2, 357.1; m/z found, 358.2 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 8.18 (br s, 1H), 8.08 (d, J=8.2 Hz, 2H), 7.82 (br d, J=8.0 Hz, 1H), 7.64 (br s, 1H), 7.56 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.0 Hz, 2H), 7.35 (t, J=7.5 Hz, 2H), 7.28-7.25 (m, 1H), 5.39 (s, 1H), 3.40 (s, 3H).

Workup

customOrganics were removed under reduced pressure, and purification

Sources & evidence

ORD record: ord-4463ef3fef0d490ba038f87cb326af15
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687639B2

Reaction notes

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