Sodium Bicarbonate → 5-(Benzoxazol-2-yl)-1-(4-methoxycarbonylphenylmethyl)-2-methylbenzimidazole

HRID 74299Notes

Reaction equation

HRID 74299 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[O:21][C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)=[CH:16][C:14]=2[NH2:15])=[CH:7][CH:6]=1)=[O:4].Cl.[C:30](=N)(OC)[CH3:31].C(=O)([O-])O.[Na+]>CO>[O:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[C:17]1[CH:18]=[CH:19][C:13]2[N:12]([CH2:11][C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=3)[C:30]([CH3:31])=[N:15][C:14]=2[CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674985672-(2-(4-Methoxycarbonylphenylmethyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674988695-(Benzoxazol-2-yl)-1-(4-methoxycarbonylphenylmethyl)-2-methylbenzimidazoleYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-(4-methoxycarbonylphenylmethyl)aminoanilin-5-yl)benzoxazole (see Working Example 113-2) (59.0 mg, 0.159 mmol) in methanol (3 mL) was added methyl acetimidate hydrochloride (19 mg, 0.174 mmol), and this was heated to reflux for 1.5 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was stirred for several minutes at room temperature. The crystals obtained were filtered, and after being washed with water, they were dried to yield the title compound (62.2 mg, 98% yield) as yellow crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 1.5 hours
  3. customThe crystals obtained
  4. filtrationwere filtered
  5. washafter being washed with water, they
  6. customwere dried

Sources & evidence

ORD record
ord-b7ff4d4c6580482bae322519dd1eab08
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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