Calcium Hydroxide → HCID 72700428, compound

HRID 591386Notes

Reaction equation

HRID 591386 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-].[Ca+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.[Ca+2:40]

Participants

5

Reactant 2

HCID 6093208Calcium HydroxideHCID 72543758HCID 72543758, compound

Product 1

HCID 72700428HCID 72700428, compoundYield 88.6%

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) (0.200 g, 0.365 mmol) in ethanol (5 mL) was added calcium hydroxide (0.041 g, 0.55 mmol) in 2 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 (2×10 mL), acetone (2×10 mL) and acetonitrile (2×15 mL) to afford calcium (5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonylphosphoramidate (7) (0.195 g, 0.322 mmol, 88.6% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 4.77 (d, J=4.27 Hz, 2H), 6.92 (t, J=4.14 Hz, 1H), 7.26-7.35 (m, 2H), 7.39 (d, J=8.03 Hz, 1H), 7.50-7.60 (m, 5H), 7.79 (td, J=7.65, 1.76 Hz, 1H), 7.83-7.89 (m, 1H), 7.91-7.96 (m, 1H), 8.30 (d, J=4.27 Hz, 1H), 9.10 (s, 1H), 9.25 (t, J=2.13 Hz, 1H), 9.73 (d, J=2.01 Hz, 1H); LCMS Method I: retention time 1.66 min, [M−1]=547. HPLC Method B: Purity 94.3%, retention time 6.17 min, HPLC Method C: Purity 94.45%, retention time 5.97 min. Elemental analysis: Compound was hygroscopic, elemental analysis not obtained.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washthe residue was washed with ethyl acetate (2×10 mL), acetone (2×10 mL) and acetonitrile (2×15 mL)

Sources & evidence

ORD record
ord-3b396a1a2167440e89f890aace3a1273
Source dataset
uspto-grants-2016_01
Patent number
US09238666B2

Reaction notes

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