Phenyl chloroformate → HCID 59380121, compound

HRID 2353746Notes

Reaction equation

HRID 2353746 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[F:11][C:12]1[CH:13]=[C:14]([S:19]([C:22]([C:25]2[CH:30]=[C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]3[CH3:37])[N:28]=[C:27]([C:38]3[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=3)[N:26]=2)([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH:15]=[C:16]([F:18])[CH:17]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[F:18][C:16]1[CH:15]=[C:14]([S:19]([C:22]([C:25]2[CH:30]=[C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]3[CH3:37])[N:28]=[C:27]([C:38]3[CH:39]=[CH:40][C:41]([NH:42][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:43][CH:44]=3)[N:26]=2)([CH3:23])[CH3:24])(=[O:20])=[O:21])[CH:13]=[C:12]([F:11])[CH:17]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380104HCID 59380104, compound

Product 1

HCID 59380121HCID 59380121, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.413 mL, 3.29 mmol) was added to 4-[4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (1.46 g, 2.99 mmol) and sodium hydrogen carbonate (0.377 g, 4.48 mmol) in dioxane (25 mL). The resulting slurry was stirred at RT for 1 hour. The 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 25%-80% ethyl acetate in isohexane, to give a colourless gum. This material was triturated with diethyl ether to give the desired material as a colourless crystalline solid (1.808 g).

Workup

  1. customThe 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 25%-80% ethyl acetate in isohexane
  7. customto give a colourless gum
  8. customThis material was triturated with diethyl ether

Sources & evidence

ORD record
ord-3fcc8259b2404d789e920ceb07662dcc
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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