Phenyl chloroformate → HCID 59380086, compound

HRID 2353759Notes

Reaction equation

HRID 2353759 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]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:27])=[O:26])[N:21]=[C:20]([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=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]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:26])=[O:27])[N:21]=[C:20]([C:34]2[CH:35]=[CH:36][C:37]([NH:38][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:39][CH:40]=2)[N:19]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379985HCID 59379985, compound

Product 1

HCID 59380086HCID 59380086, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.390 mL, 3.10 mmol) was added to 4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(pyridin-2-ylsulfonylmethyl)pyrimidin-2-yl]aniline (1.1 g, 2.59 mmol) and sodium hydrogen carbonate (0.434 g, 5.17 mmol) in dioxane (25 mL) at RT. The resulting slurry was stirred at RT for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic solution was separated, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash silica chromatography using gradient elution 0%-20% ethyl acetate in DCM, to give the desired material as a yellow foam (1.130 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic solution was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica chromatography
  6. washelution 0%-20% ethyl acetate in DCM

Sources & evidence

ORD record
ord-2598dc2867544ec7b273a657e15cdcd9
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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