Hydrochloric Acid → HCID 18985278, compound

HRID 1440026Notes

Reaction equation

HRID 1440026 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]([CH:24]([O:27][CH3:28])[O:25][CH3:26])[CH2:10][CH2:11][CH2:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=2)=[C:4]([NH2:29])[N:3]=1.[OH-].[Na+].Cl>O1CCCC1.O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:29])[C:5]([CH:9]([CH:24]([O:27][CH3:28])[O:25][CH3:26])[CH2:10][CH2:11][CH2:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18985293HCID 18985293, compound

Product 1

HCID 18985278HCID 18985278, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

The product of Example 13 (403 mg) was suspended in a mixed solution of tetrahydrofuran-water (5:1, 8.0 ml), 1N aqueous solution of sodium hydroxide (2.0 ml) was added thereto and the mixture was stirred at 40° C. overnight. After neutralizing the mixture by adding 1N hydrochloric acid (2.0 ml), solvent was removed by distillation under reduced pressure and the residue was dried to give crude 4-[4-(2,4,6-triaminopyrimidin-5-yl)-5,5-dimethoxypentyl]benzoic acid. The total amount of the crude product and diethyl glutamate hydrochloride (360 mg) were suspended in dimethylformamide (4.0 ml), a solution (4.0 ml) of diethyl phosphorocyanidate (171 mg) in dimethylformamide was added thereto at 0° C. and the mixture was stirred. Subsequently, a solution (4.0 ml) of triethylamine (303 mg) in dimethylformamide was added dropwise thereto at the same temperature and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 3 hours, followed by removing solvent by distillation under reduced pressure. The resulting residue was purified by flash column chromatography (15 g of silica gel; dichloromethane-methano 30:1→75:1) to give the subject compound (417 mg).

Workup

  1. additionwas added
  2. customwas removed by distillation under reduced pressure
  3. customthe residue was dried

Sources & evidence

ORD record
ord-293e6fbc911c489d9a547ed0b28d9ec5
Source dataset
uspto-grants-1996_03
Patent number
US05496946

Reaction notes

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