Morpholine → HCID 178493056, compound

HRID 989311Notes

Reaction equation

HRID 989311 reaction equation
ClC[C:3]1[N:4]=[C:5]2[CH2:14][C:13]3[N:12]=[CH:11][C:10]([C:15]#[N:16])=[C:9]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[C:8]=3[CH:7]=[C:6]2[N:30]=1.N1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:25][O:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([O:28][CH3:29])[C:21]=1[O:26][CH3:27])[NH:17][C:9]1[C:8]2[CH:7]=[C:6]3[N:30]=[CH:3][NH:4][C:5]3=[CH:14][C:13]=2[N:12]=[CH:11][C:10]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 69372248HCID 69372248, compound

Product 1

HCID 178493056HCID 178493056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.09 g (0.2 mmol) of 2-(chloromethyl)-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, 0.2 mL (2.3 mmol) of morpholine and 0.3 g (2.2 mmol) of anhydrous potassium carbonate in 5 mL of ethanol is stirred at room temperature overnight. The product mixture is filtered to remove the inorganic salts and the filtrate is evaporated to dryness to yield an oil. The oil is purified by silica gel chromatography utilizing a gradient of methylene chloride/methanol(97:3 to 90:10) to yield 0.087 g of 2-(4-morpholinylmethyl)-8-(3,4,5-trimethoxyanilino)-3H-imidazo[4,5-g]quinoline-ylmethyl)-8-(3,4,5-trimethoxyanilino)-3H-imidazo[4,5-g]quinoline-7-carbonitrile as a yellow solid, mp 258-260° C. (dec).

Workup

  1. filtrationThe product mixture is filtered
  2. customto remove the inorganic salts
  3. customthe filtrate is evaporated to dryness
  4. customto yield an oil
  5. customThe oil is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f58a165b83ce41a6ae581df9bbec621c
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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