Toluene → HCID 58864281, compound

HRID 1353547Notes

Reaction equation

HRID 1353547 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[CH3:12][O:13][C:14](=[O:28])[C@H:15]([NH2:27])[CH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH2:20]2.[NH:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[NH:37][C:36]2=[O:45])[CH2:31][CH2:30]1>C(Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH3:12][O:13][C:14](=[O:28])[C@H:15]([NH:27][C:1]([N:29]1[CH2:30][CH2:31][CH:32]([N:35]2[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[NH:37][C:36]2=[O:45])[CH2:33][CH2:34]1)=[O:2])[CH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH2:20]2

Participants

8

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 58864366HCID 58864366, compound

Product 1

HCID 58864281HCID 58864281, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of phosgene in toluene (2M, 0.158 mL, 0.30 mmol) was added to a vigorously stirred mixture of (R)-2-amino-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)-propionic acid methyl ester (70 mg, 0.25 mmol) in methylene chloride (15 mL) and saturated sodium bicarbonate (7.5 mL). After the mixture was stirred at room temperature for 30 min, 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (58 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for 1.5 h, diluted with ethyl acetate, and washed with 0.25 N hydrochloric acid that had been saturated with solid sodium chloride. The organic layers were dried over sodium sulfate. After filtration, solvents were removed to afford the title compound as a tan viscous oil. LC/MS: tR=2.01 min, 492.10 (MH)+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1.5 h
  2. washwashed with 0.25 N hydrochloric acid that
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. filtrationAfter filtration, solvents
  5. customwere removed

Sources & evidence

ORD record
ord-5329a0d2f06143479de7ea14ec98aaee
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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