Magnesium Hydroxide → HCID 72700513, compound

HRID 591387Notes

Reaction equation

HRID 591387 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[N:10][C:11]([C:17]2[CH:18]=[C:19]([S:23]([NH:26][P:27](=[O:30])([OH:29])[OH:28])(=[O:25])=[O:24])[CH:20]=[N:21][CH:22]=2)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Mg+2:40].[OH-]>C(O)C.O>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[N:10][C:11]([C:17]2[CH:18]=[C:19]([S:23]([NH:26][P:27](=[O:28])([O-:29])[O-:30])(=[O:24])=[O:25])[CH:20]=[N:21][CH:22]=2)=[N:12]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[Mg+2:40]

Participants

5

Reactant 2

HCID 73981Magnesium HydroxideHCID 72543758HCID 72543758, compound

Product 1

HCID 72700513HCID 72700513, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of ((5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonyl)phosphoramidic acid (2) (0.050 g, 0.091 mmol) in ethanol (5 mL) was added magnesium hydroxide (7.97 mg, 0.137 mmol) in 1 mL of water. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 2 h. The reaction mixture was concentrated to dryness and the residue was washed with ethyl acetate (2×5 mL), acetone (2×10 mL) and acetonitrile (2×10 mL) to afford magnesium(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonylphosphoramidate (8) (0.040 g, 0.069 mmol, 76% yield) as a yellow solid. 1H NMR was not taken because of poor solubility. LCMS Method I: retention time 1.66 min, [M−1]=547. HPLC Method B: Purity 98.1%, retention time 6.18 min, HPLC Method C: Purity 95.6%, retention time 5.98 min. Elemental analysis: MF C25H20N6SPO5.Mg H2O, Calculated C, 46.15; H, 4.41; N, 12.92; Mg, 4.15; H2O, 11.70. Found C, 40.66; H, 4.12; N, 11.23; Mg, 4.14; H2O, 11.70; C and N are not in agreement.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washthe residue was washed with ethyl acetate (2×5 mL), acetone (2×10 mL) and acetonitrile (2×10 mL)

Sources & evidence

ORD record
ord-e363aea318994cc2b5a80ee3509a01d6
Source dataset
uspto-grants-2016_01
Patent number
US09238666B2

Reaction notes

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