Sodium Bicarbonate → HCID 18536391, compound

HRID 412556Notes

Reaction equation

HRID 412556 reaction equation
[ClH:1].Cl.[NH:3]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:32]=[CH:31][C:12]([O:13][CH2:14][C:15]3[N:19]([CH2:20][CH2:21][O:22][CH3:23])[C:18]4[CH:24]=[CH:25][C:26]([C:28]([NH2:30])=[NH:29])=[CH:27][C:17]=4[N:16]=3)=[CH:11][CH:10]=2)[CH2:4]1.C(=O)([O-])O.[Na+].Cl.[C:39](=[NH:44])(OCC)[CH3:40]>O1CCCC1.O>[ClH:1].[ClH:1].[C:39]([N:3]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]3[N:19]([CH2:20][CH2:21][O:22][CH3:23])[C:18]4[CH:24]=[CH:25][C:26]([C:28]([NH2:30])=[NH:29])=[CH:27][C:17]=4[N:16]=3)=[CH:31][CH:32]=2)[CH2:4]1)(=[NH:44])[CH3:40]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18536351HCID 18536351, compound

Product 1

HCID 18536391HCID 18536391, compoundYield 167.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(pyrrolidin-3-yloxy)phenoxymethyl]-1-(2-methoxyethyl)benzimidazole-5-carboxamidine dihydrochloride (44 mg) in a mixture of tetrahydrofuran (2 ml) and water (0.6 ml) were added sodium hydrogencarbonate (38 mg), and ethyl acetoimidate hydrochloride (33 mg), and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, insoluble material was removed and the solvent was evaporated. The obtained residue was separated by HPLC (50% methanol-water, 0.05% trifluoroacetic acid). To the obtained residue was added dil. hydrochloric acid and the solvent was evaporated and dried under reduced pressure to give the title compound (40 mg).

Workup

  1. customAfter completion of the reaction, insoluble material
  2. customwas removed
  3. customthe solvent was evaporated
  4. customThe obtained residue was separated by HPLC (50% methanol-water, 0.05% trifluoroacetic acid)
  5. additionTo the obtained residue was added dil. hydrochloric acid
  6. customthe solvent was evaporated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-122840d3412e47be95388698c435f833
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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