Potassium Hydroxide → HCID 131734518, compound

HRID 591385Notes

Reaction equation

HRID 591385 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-].[K+:40]>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.[K+:40].[K+:40].[K+:40]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 72543758HCID 72543758, compound

Product 1

HCID 131734518HCID 131734518, compoundYield 80.6%

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) (0.030 g, 0.054 mmol) in ethanol (3 mL) was added KOH (9.0 mg, 0.16 mmol) in 0.5 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 (2×8 mL), acetone (2×8 mL) and acetonitrile (2×8 mL) to afford tri-potassium(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonylphosphoramidate (6) (0.028 g, 0.043 mmol, 78% yield) as a brown solid. 1H NMR (400 MHz, deuterium oxide) δ ppm 4.52 (s, 2H), 7.09 (d, J=7.78 Hz, 1H), 7.19-7.24 (m, 2H), 7.28-7.40 (m, 5H), 7.61-7.77 (m, 3H), 8.28 (d, J=4.27 Hz, 1H), 8.91 (t, J=1.88 Hz, 1H), 9.08 (d, J=2.26 Hz, 1H), 9.21 (d, J=1.76 Hz, 1H); LCMS Method A: retention time 1.60 min, [M+1]=549.2. HPLC Method B: Purity 96.0%, retention time 6.09 min, HPLC Method C: Purity 96.0%, retention time 5.86 min. Elemental analysis: MF C25H18N6SPO5.2.6 K.4.5 H2O, Calculated C 41.22; H, 3.72; N, 11.54; K, 14.12; H2O, 11.00; Found C, 40.79; H, 3.56; N, 11.17; K, 13.76; H2O, 10.49.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washthe residue was washed with ethyl acetate (2×8 mL), acetone (2×8 mL) and acetonitrile (2×8 mL)

Sources & evidence

ORD record
ord-86ec1997b3e14e0b99bf2b639be5cc41
Source dataset
uspto-grants-2016_01
Patent number
US09238666B2

Reaction notes

Loading…