Phenyl chloroformate → HCID 59380114, compound

HRID 2353714Notes

Reaction equation

HRID 2353714 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:14]([C:17]([C:20]2[CH:25]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]3[CH3:32])[N:23]=[C:22]([C:33]3[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=3)[N:21]=2)([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH:11]1([S:14]([C:17]([C:20]2[CH:25]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]3[CH3:32])[N:23]=[C:22]([C:33]3[CH:39]=[CH:38][C:36]([NH:37][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:35][CH:34]=3)[N:21]=2)([CH3:18])[CH3:19])(=[O:15])=[O:16])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380128HCID 59380128, compound

Product 1

HCID 59380114HCID 59380114, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.215 mL, 1.71 mmol) was added dropwise to 4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (712 mg, 1.71 mmol) and sodium bicarbonate (215 mg, 2.56 mmol) in dioxane (15 mL) under nitrogen. The resulting suspension was stirred at RT for 2 hours. The reaction mixture was evaporated to dryness and redissolved in ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was dried (MgSO4), filtered and evaporated to give the desired material (983 mg).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in ethyl acetate (100 mL)
  3. washwashed with water (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c501354d753440d5b33478d300aaf759
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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