Tetrahydrofuran → ethyl 3-(3,4-dimethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

HRID 644376Notes

Reaction equation

HRID 644376 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][C:24]2=[O:33])[CH2:19][CH2:18]1.C1C[O:37][CH2:36]C1>>[CH3:16][C:11]1[CH:10]=[C:9]([CH2:8][CH:2]([NH:1][C:36]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:33])[CH2:21][CH2:22]2)=[O:37])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:13][C:12]=1[CH3:15]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 22507395Ethyl 2-amino-3-(3,4-dimethylphenyl)propanoate

Product 1

HCID 68579013ethyl 3-(3,4-dimethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

Procedure

10.0 g (57.9 mmol) CDT were added to the solution of 11.0 g (49.7 mmol) ethyl 2-amino-3-(3,4-dimethyl-phenyl)-propionate in 250 mL THF cooled in the ice bath, stirred for 1 h while cooling with an ice bath and for 1 h at RT. Then 12.7 g (54.7 mmol) 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one was added, the reaction mixture was refluxed for 2.5 h and evaporated down under reduced pressure. The residue was distributed between saturated NaHCO3 solution and EtOAc and the aqueous phase was extracted twice more with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated down under reduced pressure.

Workup

  1. temperaturethe reaction mixture was refluxed for 2.5 h
  2. customevaporated down under reduced pressure
  3. extractionthe aqueous phase was extracted twice more with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-78c1b66940a34190b3c6014232e7135f
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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