Phenyl chloroformate → HCID 59379979, compound

HRID 2353757Notes

Reaction equation

HRID 2353757 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]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)(=[O:29])=[O:28])([CH3:26])[CH3:25])[N:21]=[C:20]([C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=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]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)(=[O:28])=[O:29])([CH3:26])[CH3:25])[N:21]=[C:20]([C:36]2[CH:37]=[CH:38][C:39]([NH:40][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:41][CH:42]=2)[N:19]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380069HCID 59380069, compound

Product 1

HCID 59379979HCID 59379979, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.432 mL, 3.44 mmol) was added to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-pyridin-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]aniline (1.3 g, 2.87 mmol) and sodium hydrogen carbonate (0.482 g, 5.73 mmol) in dioxane (20 mL) at RT. The resulting slurry was stirred at RT for 1 hour and then the reaction 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 0%-20% ethyl acetate in DCM, to give the desired material as a yellow dry film (1.62 g).

Workup

  1. customthe reaction 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 0%-20% ethyl acetate in DCM

Sources & evidence

ORD record
ord-653d12192d9142f4951a2a31ce424864
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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