Phenyl chloroformate → HCID 59380218, compound

HRID 2353750Notes

Reaction equation

HRID 2353750 reaction equation
[CH:1]1([S:7]([C:10]([C:13]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[N:16]=[C:15]([C:26]3[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=3)[N:14]=2)([CH3:12])[CH3:11])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].Cl[C:39]([O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:40]>O1CCOCC1>[CH:1]1([S:7]([C:10]([C:13]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[N:16]=[C:15]([C:26]3[CH:32]=[CH:31][C:29]([NH:30][C:39](=[O:40])[O:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[CH:28][CH:27]=3)[N:14]=2)([CH3:11])[CH3:12])(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380190HCID 59380190, compound

Product 1

HCID 59380218HCID 59380218, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[4-(2-cyclohexylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (1.1 g, 2.40 mmol) in 1,4-dioxane (12 mL) was added sodium bicarbonate (0.302 g, 3.60 mmol). Phenyl chloroformate (0.316 mL, 2.52 mmol) was then added dropwise and the resulting mixture was stirred at RT for 3 hours. The resulting mixture was evaporated to dryness and the residue partitioned between water (10 mL) and DCM (10 mL). The organic layer was separated and evaporated to dryness. The residue was triturated with diethyl ether to give the desired material as a solid (1.328 g).

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. customthe residue partitioned between water (10 mL) and DCM (10 mL)
  3. customThe organic layer was separated
  4. customevaporated to dryness
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-27f85cda911a4b7a8dae136f5d7abfba
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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