1,1'-Carbonyldiimidazole → HCID 53712764, compound

HRID 2232571Notes

Reaction equation

HRID 2232571 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][CH:14]([CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:20]=1)[C:15]([OH:17])=O.[CH3:35][NH:36][CH:37]([CH3:39])[CH3:38]>O1CCCC1>[CH:37]([N:36]([CH3:35])[C:15](=[O:17])[CH:14]([CH3:13])[CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[C:21]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:20]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78485N-Methylisopropylamine2×HCID 9811219HCID 9811219, compound

Product 1

HCID 53712764HCID 53712764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (1.65 g) is added to a stirred solution of dextrorotatory α-methyl-2-phenyl-4-quinazolinepropanoic acid (2 g) in tetrahydrofuran (20 cc). The mixture is stirred for one hour at room temperature (until the evolution of gas has ceased) and N-methylisopropylamine (1.03 cc) is then added. The mixture is stirred for three days at room temperature (approximately 20° C.), then heated under reflux for 6 hours, N-methylisopropylamine (1.03 cc) is added and the mixture is heated under reflux for a further 12 hours. The treatment is then similar to that described in Example 85. After two recrystallizations in acetonitrile, laevorotatory N-isopropyl-N-methyl-α-methyl-2-phenyl-4-quinazolinepropanamide (19 g), m.p. 171.2° C., is isolated; αD at 0.5% in EtOH at 23° C.=-12.1°±2°.

Workup

  1. additionis then added
  2. stirringThe mixture is stirred for three days at room temperature (approximately 20° C.)
  3. temperatureheated
  4. temperatureunder reflux for 6 hours
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for a further 12 hours
  7. customAfter two recrystallizations in acetonitrile

Sources & evidence

ORD record
ord-e54e48421c4c4a55bcc280e124e21330
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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