Ammonia → HCID 10194183, compound

HRID 2181703Notes

Reaction equation

HRID 2181703 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:21][C:22]1[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=O)=[CH:24][CH:23]=1.C(Cl)(=O)C(Cl)=O.[NH3:41]>ClCCl.CN(C=O)C.O1CCOCC1>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH2:41])=[O:28])=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 22482199HCID 22482199, compound

Product 1

HCID 10194183HCID 10194183, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.1 g (0.254 mmol) of the compound of Example 18 is suspended in 50 ml of dichloromethane. 35.4 mg of oxalyl chloride (0.279 mmol) is added, followed by 1 drop of DMF. The reaction is refluxed under nitrogen for 2 hours, and stirred at room temperature for an additional 12 hours. Then an excess amount of 0.5 M ammonia in dioxane is added. The reaction is stirred at room temperature for 1 hour. The solvent is then removed in vacuum and the residue is washed with 1:1 water:methanol to yield 70 mg of an off-white powder as the desired product.

Workup

  1. temperatureThe reaction is refluxed under nitrogen for 2 hours
  2. stirringThe reaction is stirred at room temperature for 1 hour
  3. customThe solvent is then removed in vacuum
  4. washthe residue is washed with 1:1 water

Sources & evidence

ORD record
ord-4db4b627be2e4494a87c53630e9e7293
Source dataset
uspto-grants-2005_05
Patent number
US06894057B2

Reaction notes

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