Methanol → HCID 178487586, compound

HRID 492202Notes

Reaction equation

HRID 492202 reaction equation
[Na].CO.[ClH:4].[NH2:5][C:6]([NH2:8])=[NH:7].[Cl:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[N:14]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH:13]=1)=[O:11]>COCCOC>[ClH:9].[ClH:4].[NH:7]([C:10]([C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[N:14]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH:13]=1)=[O:11])[C:6]([NH2:8])=[NH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 713779096-Methoxy-1-(quinolin-4-yl)-1H-indole-3-carbonyl chloride

Product 1

HCID 178487586HCID 178487586, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
22 °C

Procedure

0.87 g (38 mmol) of sodium is added at a temperature in the region of 22° C. under an argon atmosphere to 60 cm3 of methanol. After complete dissolution, 3.6 g (37.5 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 22° C. for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is suspended in 60 cm3 of 1,2-dimethoxyethane. 2.4 g (7.13 mmol) of 3-chlorocarbonyl-6-methoxy-1-(quinol-4-yl)-1H-indole are subsequently added at a temperature in the region of 22° C. under an argon atmosphere. After stirring at reflux for 18 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is triturated in 100 cm3 of water. The suspension is filtered and dried to give a beige-coloured powder which is purified by silica gel chromatography [eluent: dichloromethane/methanol (85/15 by volume)]. After concentrating the fractions under reduced pressure (2.7 kPa), 1.7 g of a beige-coloured foam are obtained, which foam is triturated in 60 cm3 of N hydrochloric acid to provide, after filtration, 1.86 g of 3-guanidinocarbonyl-6-methoxy-1-(quinol-4-yl)-1H-indole dihydrochloride in the form of yellow crystals melting at a temperature of greater than 260° C. Mass spectrum (EI): m/e 359 (M+·), m/e 301. IR spectrum (KBr): 3356, 2587, 1694, 1630, 1595, 1542, 1495, 1441, 1261, 1232, 1192, 823 and 763 cm−1.

Workup

  1. additionare added
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. stirringAfter stirring
  5. temperatureat reflux for 18 hours
  6. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customto give a residue which
  8. customis triturated in 100 cm3 of water
  9. filtrationThe suspension is filtered
  10. customdried
  11. customto give a beige-coloured powder which
  12. customis purified by silica gel chromatography [eluent: dichloromethane/methanol (85/15 by volume)]
  13. concentrationAfter concentrating the fractions under reduced pressure (2.7 kPa), 1.7 g of a beige-coloured foam
  14. customare obtained
  15. customwhich foam is triturated in 60 cm3 of N hydrochloric acid
  16. customto provide
  17. filtrationafter filtration, 1.86 g of 3-guanidinocarbonyl-6-methoxy-1-(quinol-4-yl)-1H-indole dihydrochloride in the form of yellow crystals
  18. custommelting at a temperature of greater than 260° C

Sources & evidence

ORD record
ord-a324eead70f14224828085134c9145fc
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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