1,1'-Carbonyldiimidazole → HCID 23302336, compound

HRID 1953249Notes

Reaction equation

HRID 1953249 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=O)=[CH:5][CH:4]=1)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:25]1([N:35]([CH3:47])[C:36]([C:38]2[CH:39]=[CH:40][C:41]([NH:45][CH3:46])=[C:42]([CH:44]=2)[NH2:43])=[O:37])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH3:47][N:35]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[C:36]([C:38]1[CH:39]=[CH:40][C:41]2[N:45]([CH3:46])[C:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[N:43][C:42]=2[CH:44]=1)=[O:37]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 795874-Cyanophenylacetic acidHCID 23302672HCID 23302672, compound

Product 1

HCID 23302336HCID 23302336, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

483 mg (3.0 mmol) of 4-cyanophenylacetic acid and 486 mg (3.0 mmol) of carbonyldiimidazole are dissolved in 20 ml tetrahydrofuran and stirred for 1 hour at 50° C. Then 916 mg 5-(naphthalen-1-yl-methylaminocarbonyl)-2-methylamino-aniline are added thereto and stirring is continued for a further 3 hours at 50° C. The solvent is concentrated by evaporation, the residue is combined with 30 ml glacial acetic acid and refluxed for 1 hour. After evaporation of the solvent the filtrate is chromatographed on silica gel, eluting with methylene chloride/ethanol 99:1, 98:1 and 97:1. The desired fractions are concentrated by evaporation, the residue is triturated with acetone/ether, suction filtered and dried.

Workup

  1. stirringstirring
  2. waitis continued for a further 3 hours at 50° C
  3. concentrationThe solvent is concentrated by evaporation
  4. temperaturerefluxed for 1 hour
  5. customAfter evaporation of the solvent the filtrate
  6. customis chromatographed on silica gel
  7. washeluting with methylene chloride/ethanol 99:1, 98:1 and 97:1
  8. concentrationThe desired fractions are concentrated by evaporation
  9. customthe residue is triturated with acetone/ether, suction
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-cf4db1e088634163a58e1bdeb83fb60b
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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