Phenyl chloroformate → HCID 59380129, compound

HRID 2353742Notes

Reaction equation

HRID 2353742 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]([CH3:33])([CH3:32])[CH3:31])(=[O:29])=[O:28])([CH3:26])[CH3:25])[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+]>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]([CH3:33])([CH3:32])[CH3:31])(=[O:29])=[O:28])([CH3:25])[CH3:26])[N:21]=[C:20]([C:34]2[CH:40]=[CH:39][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:36][CH:35]=2)[N:19]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379933HCID 59379933, compound

Product 1

HCID 59380129HCID 59380129, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.368 mL, 2.93 mmol) was added to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-tert-butylsulfonylpropan-2-yl)pyrimidin-2-yl]aniline (1.153 g, 2.67 mmol) and sodium hydrogen carbonate (0.336 g, 4.00 mmol) in dioxane (20 mL) at RT. The resulting slurry was stirred at RT for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed on silica, eluting with 20%-70% ethyl acetate in isohexane, to give the desired material as a near colourless solid (1.42 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica
  6. washeluting with 20%-70% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3d77e50b72614a90813a916226fb303f
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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