Acetonitrile → HCID 86738857, compound

HRID 851000Notes

Reaction equation

HRID 851000 reaction equation
[C:1]([N:4]1[CH2:8][CH:7]([O:9][C:10]([O:13][CH3:14])([CH3:12])[CH3:11])[CH2:6][CH:5]1[C:15]([NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[C:22]([C:29]([OH:31])=[O:30])=[CH:21]2)=[O:16])(=[O:3])[CH3:2].C(#N)C.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[N-:4]1[CH:5]=[CH:15][N:17]=[CH:18]1.[C:1]([N:4]1[CH2:8][CH:7]([O:9][C:10]([O:13][CH3:14])([CH3:11])[CH3:12])[CH2:6][CH:5]1[C:15]([NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[C:22]([C:29]([OH:31])=[O:30])=[CH:21]2)=[O:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 682631,1'-CarbonyldiimidazoleHCID 20503433HCID 20503433, compound

Product 1

HCID 86738857HCID 86738857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the above 6-[[[1-acetyl-4-(1-methoxy-1-methylethoxy)2-pyrrolidinyl]carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 75 ml of acetonitrile, 5 ml of dimethylformamide, and 3.47 g (24.4 mmol) carbonyldiimidazole is heated at 42°-50° for 2/3 hours and is stirred for 2 hours at room temperature. The mixture is cooled with ice and stirred overnight at room temperature. The solution is concentrated to an oil and treated with tetrahydrofuran and ether, and the solid filtered to give 1.70 g of 6-[[[1-acetyl-4-(1-methoxy-1-methylethoxy)-2-pyrrolidinyl]carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid imidazolide.

Workup

  1. temperatureis heated at 42°-50° for 2/3 hours
  2. temperatureThe mixture is cooled with ice
  3. stirringstirred overnight at room temperature
  4. concentrationThe solution is concentrated to an oil
  5. additiontreated with tetrahydrofuran and ether
  6. filtrationthe solid filtered

Sources & evidence

ORD record
ord-e0731adc921b4fbab360cbed2dbf7ad7
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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