Phenyl chloroformate → HCID 59380178, compound

HRID 2353748Notes

Reaction equation

HRID 2353748 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]([CH2:22][C:23]2[CH:28]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])[N:26]=[C:25]([C:36]3[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=3)[N:24]=2)(=[O:21])=[O:20])[CH:15]=[C:16]([F:18])[CH:17]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[F:11][C:12]1[CH:13]=[C:14]([S:19]([CH2:22][C:23]2[CH:28]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])[N:26]=[C:25]([C:36]3[CH:42]=[CH:41][C:39]([NH:40][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:38][CH:37]=3)[N:24]=2)(=[O:20])=[O:21])[CH:15]=[C:16]([F:18])[CH:17]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380212HCID 59380212, compound

Product 1

HCID 59380178HCID 59380178, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.208 mL, 1.66 mmol) was added to 4-[4-[(3,5-difluorophenyl)sulfonylmethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (693 mg, 1.50 mmol) and sodium hydrogen carbonate (190 mg, 2.26 mmol) in dioxane (10 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) and concentrated under reduced pressure. The residue was chromatographed on silica, eluting with 25%-80% ethyl acetate in isohexane, to give the desired product as a yellow dry film (827 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica
  5. washeluting with 25%-80% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3e4527983ff24172acb0e97c07802960
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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