Water → HCID 59380116, compound

HRID 2353705Notes

Reaction equation

HRID 2353705 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][CH2:14][N:13]1[C:18]1[CH:23]=[C:22]([CH2:24][S:25]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[N:21]=[C:20]([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[N:19]=1.C(=O)(O)[O-].[Na+].O>O1CCOCC1>[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][CH2:14][N:13]1[C:18]1[CH:23]=[C:22]([CH2:24][S:25]([C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)(=[O:26])=[O:27])[N:21]=[C:20]([C:34]2[CH:35]=[CH:36][C:37]([NH:38][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:39][CH:40]=2)[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformate2×HCID 516892Sodium BicarbonateHCID 59379878HCID 59379878, compound

Product 1

HCID 59380116HCID 59380116, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.029 mL, 0.23 mmol) was added to a solution of 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]aniline (0.097 g, 0.23 mmol) and sodium bicarbonate (0.029 g, 0.34 mmol) in dioxane at RT. The resulting slurry was stirred at RT for 2 hours. Additional phenyl chloroformate (2×0.005 mL) was added to drive the reaction to completion. Water was then added to the reaction and the solid filtered, and dried in a vacuum oven to give the desired material as an off-white solid (0.098 g).

Workup

  1. customthe reaction to completion
  2. filtrationthe solid filtered
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c25f0e3544f343c88a1b90f9dbe91d03
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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