Phenyl chloroformate → HCID 59380094, compound

HRID 2353737Notes

Reaction equation

HRID 2353737 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][C:31]=2[C:36]([F:39])([F:38])[F:37])(=[O:29])=[O:28])([CH3:26])[CH3:25])[N:21]=[C:20]([C:40]2[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=2)[N:19]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.C(OCC)(=O)C>[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][C:31]=2[C:36]([F:37])([F:38])[F:39])(=[O:29])=[O:28])([CH3:25])[CH3:26])[N:21]=[C:20]([C:40]2[CH:41]=[CH:42][C:43]([NH:44][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:45][CH:46]=2)[N:19]=1

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380082HCID 59380082, compound

Product 1

HCID 59380094HCID 59380094, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.542 mL, 4.32 mmol) was added to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-[2-[2-(trifluoromethyl)phenyl]sulfonylpropan-2-yl]pyrimidin-2-yl]aniline line (1.5 g, 2.88 mmol) and sodium hydrogen carbonate (0.363 g, 4.32 mmol) in dioxane (20 mL) at 5° C. under nitrogen. The resulting mixture was stirred at RT for 2 hours then diluted with ethyl acetate (200 mL), and washed with water (125 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product which was triturated with a mixture of diethyl ether and isohexane to give the desired material as a white solid (1.38 g).

Workup

  1. washwashed with water (125 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product which
  6. customwas triturated with a mixture of diethyl ether and isohexane

Sources & evidence

ORD record
ord-e5c4c347788a4ce2bdada634c3682d94
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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