Phenyl chloroformate → HCID 59380169, compound

HRID 2353734Notes

Reaction equation

HRID 2353734 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH:11]1([S:16]([C:19]([C:22]2[CH:27]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]3[CH3:34])[N:25]=[C:24]([C:35]3[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=3)[N:23]=2)([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])O.[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH:11]1([S:16]([C:19]([C:22]2[CH:27]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]3[CH3:34])[N:25]=[C:24]([C:35]3[CH:36]=[CH:37][C:38]([NH:39][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:40][CH:41]=3)[N:23]=2)([CH3:20])[CH3:21])(=[O:17])=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379928HCID 59379928, compound

Product 1

HCID 59380169HCID 59380169, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.635 mL, 5.06 mmol) was added to 4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (1.5 g, 3.37 mmol) and sodium hydrogen carbonate (0.425 g, 5.06 mmol) in dioxane (20 mL) at 5° C. under nitrogen. The resulting mixture was stirred at RT for 2 hours. The reaction mixture was diluted with ethyl acetate (200 mL), and washed with water (125 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product which was triturated with a mixture of diethyl ether and isohexane to give the desired material as a white solid (1.30 g).

Workup

  1. washwashed with water (125 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product which
  6. customwas triturated with a mixture of diethyl ether and isohexane

Sources & evidence

ORD record
ord-61439f90bafe4e2184590e0fe27954b1
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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