Phenyl chloroformate → HCID 59380143, compound

HRID 2353744Notes

Reaction equation

HRID 2353744 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]([CH2:24][S:25]([C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:27])=[O:26])[N:21]=[C:20]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=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]([CH2:24][S:25]([C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:27])=[O:26])[N:21]=[C:20]([C:32]2[CH:38]=[CH:37][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:34][CH:33]=2)[N:19]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379942HCID 59379942, compound

Product 1

HCID 59380143HCID 59380143, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.227 mL, 1.81 mmol) was added to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(tert-butylsulfonylmethyl)pyrimidin-2-yl]aniline (665 mg, 1.64 mmol) and sodium hydrogen carbonate (207 mg, 2.47 mmol) in dioxane (12 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 material as a yellow dry film (860 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-7bfd4eac3fbe48b290a03d08c4afa972
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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