Phenyl chloroformate → HCID 58588205, compound

HRID 1361702Notes

Reaction equation

HRID 1361702 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:33](OC1C=CC=CC=1)=[O:34].[C:42]1([NH:48][CH2:49][C:50]([O:52]CC)=O)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1COCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].CO>[CH3:20][NH:19][C:15]1[N:14]=[C:13]([C:12]2[C:7]([O:6][C:5]3[CH:21]=[CH:22][C:2]([N:1]4[C:50](=[O:52])[CH2:49][N:48]([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[C:33]4=[O:34])=[CH:3][CH:4]=3)=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:18]=[CH:17][N:16]=1

Participants

9

Reactant 4

HCID 15891Phenyl chloroformateHCID 75190N-Phenylglycine ethyl esterHCID 81531DiisopropylethylamineHCID 469295414-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

Product 1

HCID 58588205HCID 58588205, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a slurry of 4-(2-(4-amino-phenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (0.200 g, 0.682 mmol) and diisopropylethylamine (0.130 mL, 0.750 mmol) in THF (2 mL) under nitrogen was added phenyl chloroformate (0.100 mL, 0.682 mmol). After 30 min, ethyl 2-(phenylamino)acetate (0.244 g, 1.36 mmol) was added, and the sealed reaction was heated to 80 deg. C. for 16 h and 100 deg. C. for 8 h. The reaction was cooled to ambient temperature, and diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by silica gel chromatography, 0 to 10% MeOH/dichloromethane, to give a solid which was slurried in methanol and filtered, rinsed with diethyl ether, and dried in vacuo to give 3-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1-phenylimidazolidine-2,4-dione as an off-white solid. MS m/z=453 [M+1]+. Calc'd for C25H20N6O2: 452.47.

Workup

  1. customthe sealed reaction
  2. temperaturewas heated to 80 deg. C
  3. waitfor 16 h
  4. custom100 deg. C
  5. waitfor 8 h
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting solid was purified by silica gel chromatography, 0 to 10% MeOH/dichloromethane
  10. customto give a solid which
  11. filtrationfiltered
  12. washrinsed with diethyl ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-34a3688cdad7499b8480343956ff39f1
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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