Phenyl chloroformate → HCID 59379953, compound

HRID 2353753Notes

Reaction equation

HRID 2353753 reaction equation
C(=O)(O)[O-].[Na+].[CH:6]1([S:12]([CH2:15][C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[N:19]=[C:18]([C:29]3[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=3)[N:17]=2)(=[O:14])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Cl[C:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38]>O1CCOCC1>[CH:6]1([S:12]([CH2:15][C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[N:19]=[C:18]([C:29]3[CH:30]=[CH:31][C:32]([NH:33][C:37](=[O:38])[O:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:34][CH:35]=3)[N:17]=2)(=[O:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379988HCID 59379988, compound

Product 1

HCID 59379953HCID 59379953, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium bicarbonate (113 mg, 1.35 mmol) was added to a solution of 4-[4-(cyclohexylsulfonylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (370 mg, 0.86 mmol) in 1,4-dioxane (5 mL). Phenyl chloroformate (0.124 mL, 0.99 mmol) was added dropwise and the resultant mixture was stirred at RT for 5 hours. The resulting mixture was evaporated to dryness and the residue partitioned between DCM (5 mL) and water (5 mL). The organic layer was separated and evaporated to dryness. The crude residue was triturated with diethyl ether to give the desired material (429 mg).

Workup

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

Sources & evidence

ORD record
ord-0d59d6510c69433795ecba7a3b668e28
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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