Phenyl chloroformate → Phenyl N-[1-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-4-piperidyl]carbamate

HRID 2353673Notes

Reaction equation

HRID 2353673 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([N:19]2[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]2)[N:9]=1.C(=O)(O)[O-].[Na+].Cl[C:32]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33]>O1CCOCC1>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:16])=[O:17])[N:11]=[C:10]([N:19]2[CH2:20][CH2:21][CH:22]([NH:25][C:32](=[O:33])[O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:23][CH2:24]2)[N:9]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformate2×HCID 516892Sodium Bicarbonate2×HCID 593800761-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]piperidin-4-amine

Product 1

HCID 59380130Phenyl N-[1-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-4-piperidyl]carbamateYield 106.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]piperidin-4-amine (500 mg, 1.35 mmol) was dissolved in dioxane (10 mL). Sodium bicarbonate (171 mg, 1.50 mmol) was added. Then phenyl chloroformate (0.171 mL, 1.35 mmol) was added dropwise over 2 minutes. The slurry was stirred at RT for 3 hours. Phenyl chloroformate (0.021 mL, 0.27 mmol) and sodium bicarbonate (21 mg, 0.12 mmol) were added. Stirring at room temp was continued for 1 hour and the reaction mixture evaporated to dryness and partitioned between water (10 mL) and ethyl acetate (10 mL). The water was extracted with a second portion of ethyl acetate (10 mL). The combined organics were dried over magnesium sulfate and evaporated to give the desired material as a foam (701 mg).

Workup

  1. stirringStirring at room temp
  2. waitwas continued for 1 hour
  3. customthe reaction mixture evaporated to dryness
  4. custompartitioned between water (10 mL) and ethyl acetate (10 mL)
  5. extractionThe water was extracted with a second portion of ethyl acetate (10 mL)
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d7a7922b0b164d558d9bf757adfd7248
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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