Phenyl chloroformate → HCID 68708966, compound

HRID 2353733Notes

Reaction equation

HRID 2353733 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]([S:13]([CH2:16][C:17]1[CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]2[CH3:29])[N:20]=[C:19]([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)[N:18]=1)(=[O:15])=[O:14])[CH3:12].C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:11]([S:13]([CH2:16][C:17]1[CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]2[CH3:29])[N:20]=[C:19]([C:30]2[CH:31]=[CH:32][C:33]([NH:34][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:35][CH:36]=2)[N:18]=1)(=[O:14])=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379974HCID 59379974, compound

Product 1

HCID 68708966HCID 68708966, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.207 mL, 1.65 mmol) was added dropwise to 4-[4-(ethylsulfonylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (620 mg, 1.65 mmol) and sodium bicarbonate (208 mg, 2.47 mmol) in dioxane (15 mL) under nitrogen. The resulting suspension was stirred at RT for 2 hours. The reaction mixture was evaporated to dryness and the residue partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was dried (MgSO4), filtered and evaporated to give the desired material as a white solid (885 mg).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-79720f4291b54e50a7efbbb504cab5a9
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…