1,1'-Carbonyldiimidazole → HCID 178523247, compound

HRID 260481Notes

Reaction equation

HRID 260481 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23](O)=[O:24])=[C:17]2[S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27].[NH2:35][CH2:36][CH2:37][C:38]1[N:42]=[CH:41][NH:40][CH:39]=1>O>[NH:40]1[CH:39]=[C:38]([CH2:37][CH2:36][NH:35][C:23]([C:18]2[NH:19][C:20]3[C:16]([C:17]=2[S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:15][C:14]([Cl:13])=[CH:22][CH:21]=3)=[O:24])[N:42]=[CH:41]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 158135163-Phenylsulfonyl-5-chloroindole-2-carboxylic acidHCID 178419017HCID 178419017, compound

Product 1

HCID 178523247HCID 178523247, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Carbonyldiimidazole (180 mg, 1.11 mmol) was added to a solution of 5-chloro-3-phenylsulfonylindole-2-carboxylic acid (Example 27, Step A) (336 mg, 0.5 mmol) cooled in an ice bath under an inert atmosphere. After 0.5 hours, histamine (125 mg, 1.12 mmol) was added to the yellow solution. After 5 hours the reaction was diluted with water and the product extracted into ethyl acetate. This organic layer was washed with dilute aq. NaHCO3, dried (Na2SO4), filtered through charcoal and the solvents evaporated. Trituration of this residue with methylene chloride gave the crude product. Crystallization from hot ethyl acetate gave analytically pure product, mp 220°-221.5° C.

Workup

  1. temperaturecooled in an ice bath under an inert atmosphere
  2. extractionthe product extracted into ethyl acetate
  3. washThis organic layer was washed with dilute aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered through charcoal
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-28f0b6c5e98d41e1a8199f69c1159297
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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