Water → HCID 59379984, compound

HRID 2353716Notes

Reaction equation

HRID 2353716 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]([C:24]([S:27]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)(=[O:29])=[O:28])([CH3:26])[CH3:25])[N:21]=[C:20]([C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=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]([C:24]([S:27]([C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)(=[O:28])=[O:29])([CH3:26])[CH3:25])[N:21]=[C:20]([C:36]2[CH:37]=[CH:38][C:39]([NH:40][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:41][CH:42]=2)[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformate2×HCID 516892Sodium BicarbonateHCID 59380031HCID 59380031, compound

Product 1

HCID 59379984HCID 59379984, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.177 mL, 1.41 mmol) was added to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidin-2-yl]aniline (0.640 g, 1.41 mmol) and sodium bicarbonate (0.178 g, 2.12 mmol) in dioxane (175 mL) at RT under air. The resulting slurry was stirred at RT for 2 hours. Two more portions of phenyl chloroformate (2×0.005 mL) were added and the reaction allowed to stir at RT. Water was then added to the reaction and the solids were filtered and dried in a vacuum oven at 55° C. overnight to give the desired material as a tan solid (0.758 g).

Workup

  1. stirringto stir at RT
  2. filtrationthe solids were filtered
  3. customdried in a vacuum oven at 55° C. overnight

Sources & evidence

ORD record
ord-a8ddd59ab90540c9907c7539535e0286
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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