Phenyl chloroformate → HCID 59380196, compound

HRID 2353715Notes

Reaction equation

HRID 2353715 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH:11]1([S:14]([CH2:17][C:18]2[CH:23]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[N:21]=[C:20]([C:31]3[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=3)[N:19]=2)(=[O:16])=[O:15])[CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH:11]1([S:14]([CH2:17][C:18]2[CH:23]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[N:21]=[C:20]([C:31]3[CH:32]=[CH:33][C:34]([NH:35][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:36][CH:37]=3)[N:19]=2)(=[O:15])=[O:16])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380127HCID 59380127, compound

Product 1

HCID 59380196HCID 59380196, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.315 mL, 2.50 mmol) was added dropwise to 4-[4-(cyclopropylsulfonylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (972 mg, 2.50 mmol) and sodium bicarbonate (315 mg, 3.75 mmol) in dioxane (20 mL). The resulting suspension was stirred at RT for 2 hours. The reaction mixture was evaporated to dryness and redissolved in ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford the desired material (1.35 g).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in ethyl acetate (100 mL)
  3. washwashed with water (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d257e0b6a9b743e4ae69d3e8245acd38
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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