Phenyl chloroformate → HCID 59380028, compound

HRID 2353731Notes

Reaction equation

HRID 2353731 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]([S:13]([C:16]([C:19]1[CH:24]=[C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]2[CH3:31])[N:22]=[C:21]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[N:20]=1)([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH3:12].C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:11]([S:13]([C:16]([C:19]1[CH:24]=[C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]2[CH3:31])[N:22]=[C:21]([C:32]2[CH:33]=[CH:34][C:35]([NH:36][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:37][CH:38]=2)[N:20]=1)([CH3:17])[CH3:18])(=[O:14])=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380168HCID 59380168, compound

Product 1

HCID 59380028HCID 59380028, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.373 mL, 2.97 mmol) was added dropwise to 4-[4-(2-ethylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (1.20 g, 2.97 mmol) and sodium bicarbonate (0.374 g, 4.45 mmol) in dioxane (25 mL) under nitrogen. The resulting suspension was stirred at RT for 2 hours. The reaction mixture was evaporated to dryness and partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was dried (MgSO4), filtered and evaporated to give the desired material as a white solid (1.40 g).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompartitioned between ethyl acetate (150 mL) and water (150 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1208bf9768174af4a957573cf78d7091
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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