Sulfur → HCID 178490287, compound

HRID 989297Notes

Reaction equation

HRID 989297 reaction equation
NC1C=C2C(=CC=1N)N=CC(C#N)=C2NC1C=C(OC)C=CC=1C.[NH2:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30]([NH:38][C:39]3[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=[CH:41][C:40]=3[CH3:47])=[C:31]([C:36]#[N:37])[CH:32]=[N:33]2)=[CH:28][C:27]=1[NH:48][C:49]([NH:51][CH2:52][CH2:53][N:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1)=S.NC1C=C2C(=CC=1NC(NCCN1CCOCC1)=S)N=CC(C#N)=C2NC1C=C(OC)C=CC=1C.[S]>O1CCOCC1.C(O)C>[CH3:46][O:45][C:43]1[CH:42]=[CH:41][C:40]([CH3:47])=[C:39]([CH:44]=1)[NH:38][C:30]1[C:29]2[CH:28]=[C:27]3[N:48]=[C:49]([NH:51][CH2:52][CH2:53][N:54]4[CH2:59][CH2:58][O:57][CH2:56][CH2:55]4)[N:25]=[C:26]3[CH2:35][C:34]=2[N:33]=[CH:32][C:31]=1[C:36]#[N:37]

Participants

7

Reactant 4

HCID 5362487SulfurHCID 18004618N-[7-amino-3-cyano-4-(5-methoxy-2-methylanilino)-6-quinolinyl]-N'-[2-(4-morpholinyl)-ethyl]thioureaHCID 219563956,7-Diamino-4-(5-methoxy-2-methylanilino)-3-quinolinecarbonitrileHCID 21956495N-[6-amino-3-cyano-4-(5-methoxy-2-methylanilino)-7-quinolinyl]-N'-[2-(4-morpholinyl)ethyl]thiourea

Product 1

HCID 178490287HCID 178490287, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.1 g (0.3 mmol) of 6,7-diamino-4-(5-methoxy-2-methylanilino)-3-quinolinecarbonitrile and 0.11 g (0.62 mmol) of 2-(4-morpholino)ethylisothiocyanate in 0.3 mL of dioxane is heated at 100° C. for 2 hours under nitrogen. The mixture is cooled and solvent is evaporated to dryness to yield an oil consisting of N-[7-amino-3-cyano-4-(5-methoxy-2-methylanilino)-6-quinolinyl]-N′-[2-(4-morpholinyl)-ethyl]thiourea and N-[6-amino-3-cyano-4-(5-methoxy-2-methylanilino)-7-quinolinyl]-N′-[2-(4-morpholinyl)ethyl]thiourea. The oil is dissolved in 3.0 mL of ethanol. To this is added 0.3 g of mercuric oxide and 20 mg of sulphur powder and the resulting mixture is heated at reflux temperature for 2 hours. The product mixture is filtered hot through diatomaceous earth, washed with methanol and solvent is evaporated to yield an oil. The oil is purified by silica gel chromatography, utilizing a gradient of methylene chloride/methanol (95:5 to 85:15) to yield 0.062 g of 8-(5-methoxy-2-methylanilino)-2-{[2-(4-morpholinyl)ethyl]amino}imidazo[4,5-g]quinoline-7-carbonitrile as a pink solid, mp 148-150° C. (shrinks at 140° C. ).

Workup

  1. temperatureThe mixture is cooled
  2. customsolvent is evaporated to dryness
  3. customto yield an oil
  4. temperaturethe resulting mixture is heated
  5. temperatureat reflux temperature for 2 hours
  6. filtrationThe product mixture is filtered hot through diatomaceous earth
  7. washwashed with methanol and solvent
  8. customis evaporated
  9. customto yield an oil
  10. customThe oil is purified by silica gel chromatography

Sources & evidence

ORD record
ord-791b6e3a15464bc0956e349c7924cb4a
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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