Acetic Acid → Methyl hydrogen [7-(3,6-dihydropyridin-1(2H)-yl)-2-oxo-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-5-yl]carbonimidate

HRID 648066Notes

Reaction equation

HRID 648066 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]2[O:10][C:11](=[O:13])[N:12]=[C:8]2[CH:7]=[C:6]([N:14]2[CH2:19][CH:18]=[CH:17][CH2:16][CH2:15]2)[N:5]=1.[CH3:20][O:21][C:22](N1C2C=CC=CC=2N=C1)=[O:23].C(O)(=O)C>CN(C)C=O>[N:14]1([C:6]2[N:5]=[C:4]([NH:3][C:22]([O:21][CH3:20])=[O:23])[N:9]3[O:10][C:11](=[O:13])[N:12]=[C:8]3[CH:7]=2)[CH2:15][CH:16]=[CH:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 12840940HCID 12840940, compoundHCID 13338974Methyl 1H-benzimidazole-1-carboxylate

Product 1

HCID 3068368Methyl hydrogen [7-(3,6-dihydropyridin-1(2H)-yl)-2-oxo-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-5-yl]carbonimidate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.2 g of sodium hydride are added portionwise to a solution, cooled to 15°, of 4.66 g of 5-amino-7-[3,6-dihydro-1(2H)-pyridyl]-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-2-one in 200 ml of dimethylformamide. The mixture is stirred vigorously at room temperature for 30 minutes. Thereafter, 5.28 g of 1-methoxycarbonylbenzimidazole in 50 ml of dimethylformamide are added thereto. After 2 hours, the mixture is treated with ice-cold water and adjusted to pH 5 with glacial acetic acid. The precipitate which results is recrystallized from methylene chloride/methanol, and there is obtained methyl 7-[3,6-dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidine-5-carbamate, m.p. 212°-214°

Workup

  1. waitAfter 2 hours
  2. additionthe mixture is treated with ice-cold water
  3. customThe precipitate which results
  4. customis recrystallized from methylene chloride/methanol

Sources & evidence

ORD record
ord-1fce8cb828d044389e7ba93de4854aee
Source dataset
uspto-grants-1983_10
Patent number
US04410698

Reaction notes

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