Phosphate → HCID 22096979, compound

HRID 1458544Notes

Reaction equation

HRID 1458544 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].P([O-])([O-])([O-])=O.[NH2:15][C:16]1[CH:17]=[C:18]([S:22]([N:25]2[CH2:30][CH:29]([C:31]([NH2:33])=[O:32])[CH2:28][CH:27]([C:34]([NH2:36])=[O:35])[CH2:26]2)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.[OH-:37].[Na+]>O1CCOCC1.CN(C)C=O.O>[Cl:3][C:2]1[N:1]=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([N:25]3[CH2:30][CH:29]([C:31](=[O:32])[NH2:33])[CH2:28][CH:27]([C:34](=[O:35])[NH2:36])[CH2:26]3)(=[O:24])=[O:23])[CH:17]=2)[N:7]=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([N:25]3[CH2:30][CH:29]([C:31](=[O:32])[NH2:33])[CH2:28][CH:27]([C:34](=[O:35])[NH2:36])[CH2:26]3)(=[O:23])=[O:37])[CH:17]=2)[N:4]=1

Participants

8

Reactant 4

HCID 1061PhosphateHCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 70048238HCID 70048238, compound

Product 1

HCID 22096979HCID 22096979, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of cyanuric chloride (280 mg, 1.5 mmol) in dioxane (5 ml) was added with stirring to phosphate buffer (10 ml, 0.3M, pH 7) at 0°-2° C. To the resulting suspension was added dropwise a solution of 1-(3-amino-benzenesulfonyl)piperidine-3,5-dicarboxylic acid diamide (Example 49, 1.0 g, 3.1 mmol) in N,N-dimethylformamide (5 ml) and the pH maintained at 6.5-7.2 by addition of 1N NaOH. After completion of the addition, the reaction mixture was warmed up to 50°-55° C. and stirred at that temperature for 2 h (until HPLC showed the completion of the reaction), then cooled to the room temperature, diluted with water, the product precipitate filtered, washed with cold water (10 ml), acetone (5 ml) and dried under vacuum at 20° C. to give 845 mg (74.2%) of the desired product; m.p.>250° C. dec; MS (ES) m/z 765.0 (M+H), MW 764.2.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction mixture was warmed up to 50°-55° C.
  3. customthe completion of the reaction),
  4. filtrationthe product precipitate filtered
  5. washwashed with cold water (10 ml), acetone (5 ml)
  6. customdried under vacuum at 20° C.

Sources & evidence

ORD record
ord-139c3e0aa0e045838ab48996ed8f47e5
Source dataset
uspto-grants-1998_12
Patent number
US05852015

Reaction notes

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