Ammonia → HCID 9935064, compound

HRID 413287Notes

Reaction equation

HRID 413287 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:11]([C:12](O)=[O:13])=[C:10]([CH2:15][N:16]3[CH2:21][CH2:20][C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)[N:9]=[CH:8]2)=[CH:4][CH:3]=1.C1N=C[N:38](C(N2C=NC=C2)=O)C=1.N.C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([C:12]([NH2:38])=[O:13])=[C:10]([CH2:15][N:16]3[CH2:21][CH2:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:18][CH2:17]3)[N:9]=[CH:8]2)=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 9805417HCID 9805417, compound

Product 1

HCID 9935064HCID 9935064, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

The product of Example 19 (0.03 g) was dissolved in N,N-dimethylformamide (2 ml), N,N-carbonyldiimidazole (0.020 g) was added and the solution heated at 60° C. for 2 hours and cooled. Aqueous ammonia solution (1 ml) was added and the mixture stirred at room temperature for 16 hours. Brine and ethyl acetate were added, the organic phase was separated, dried and the solvent removed by evaporation to give a solid. Trituration under ether gave the product as a solid (0.014 g), m.p. 227-228° C.

Workup

  1. temperaturecooled
  2. customthe organic phase was separated
  3. customdried
  4. customthe solvent removed by evaporation
  5. customto give a solid

Sources & evidence

ORD record
ord-b72fe72a344443c282b0a665ed4414e1
Source dataset
uspto-grants-2003_05
Patent number
US06566376B1

Reaction notes

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