5-Aminoimidazole-4-carboxamide hydrochloride → HCID 14677482, compound

HRID 1199952Notes

Reaction equation

HRID 1199952 reaction equation
C[N:2]([CH3:19])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=O.Cl.NC1[N:23]=[CH:24][NH:25][C:26]=1[C:27]([NH2:29])=[O:28].C(=O)(O)[O-].[Na+]>C(O)(=O)C.ClCCl>[N:13]1([C:10]2[CH:9]=[CH:8][C:7]([C:5]3[N:23]4[CH:24]=[N:25][C:26]([C:27]([NH2:29])=[O:28])=[C:19]4[N:2]=[CH:3][CH:4]=3)=[CH:12][CH:11]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 1472991HCID 1472991, compound

Product 1

HCID 14677482HCID 14677482, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 15.0 g of 3-dimethylamino-4'-morpholinoacrylophenone (prepared as described in Example 13) and 7.26 g of 4-amino-5-imidazolecarboxamide hydrochloride in 250 ml of glacial acetic acid was stirred and heated at reflux for 5 hours. The solution was evaporated in vacuo to give a black oil that was then dissolved in dichloromethane and then saturated sodium bicarbonate solution was added. A precipitate was formed which was collected by filtration as a yellow crystalline solid. The solid was triturated with ether then filtered to give 11.3 g of the product of the example as yellow crystals, mp 274°-277° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. customThe solution was evaporated in vacuo
  4. customto give a black oil that
  5. customA precipitate was formed which
  6. filtrationwas collected by filtration as a yellow crystalline solid
  7. customThe solid was triturated with ether
  8. filtrationthen filtered

Sources & evidence

ORD record
ord-80ec12fcf2da4b67a8d9fe86084d58fd
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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