Phenyl chloroformate → HCID 59379881, compound

HRID 2353760Notes

Reaction equation

HRID 2353760 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:21]([C:24]2[CH:29]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[N:27]=[C:26]([C:37]3[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=3)[N:25]=2)([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:21]([C:24]2[CH:29]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[N:27]=[C:26]([C:37]3[CH:38]=[CH:39][C:40]([NH:41][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:42][CH:43]=3)[N:25]=2)([CH3:22])[CH3:23])(=[O:19])=[O:20])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380005HCID 59380005, compound

Product 1

HCID 59379881HCID 59379881, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.256 mL, 2.04 mmol) was added dropwise to 4-[4-[2-(4-chlorophenyl)sulfonylpropan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (850 mg, 1.85 mmol) and sodium hydrogencarbonate (233 mg, 2.78 mmol) in dioxane (20 mL) at RT. The resulting suspension was stirred at RT for 2 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (2×100 mL) and saturated brine (50 mL). The organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 30 to 50% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a white solid (955 mg).

Workup

  1. washwashed with water (2×100 mL) and saturated brine (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by flash silica chromatography, elution gradient 30 to 50% ethyl acetate in isohexane
  6. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-586078a1e20c4f90a309c308cc946f1f
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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