Methanol → HCID 178479499, compound

HRID 492193Notes

Reaction equation

HRID 492193 reaction equation
[Na].CO.Cl.[NH2:5][C:6]([NH2:8])=[NH:7].Cl.[Cl:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)[CH:14]=1)=[O:12]>COCCOC>[ClH:10].[NH:7]([C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)[CH:14]=1)=[O:12])[C:6]([NH2:8])=[NH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 86596411HCID 86596411, compound

Product 1

HCID 178479499HCID 178479499, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

0.256 g (11.1 mmol) of sodium is added at 22° C. under an argon atmosphere to 40 cm3 of methanol. After complete dissolution, 1 g (10.5 mmol) of guanidine hydrochloride is added. After stirring at 22° C. for 3 hours, the reaction mixture is filtered under an argon atmosphere. The filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is dissolved in 10 cm3 of 1,2-dimethoxyethane. 1 g of 3-chlorocarbonyl-1-(quinol-6-yl)-1H-indole hydrochloride, suspended in 40 cm3 of 1,2-dimethoxyethane, is subsequently added at 22° C. under an argon atmosphere. After stirring at 22° C. for 48 hours and after 2 hours at reflux, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is triturated in 15 cm3 of water. After stirring at 22° C. for 1 hour, a few drops of 10N hydrochloric acid solution are added. After stirring at 22° C. for 12 hours, the suspension is filtered and dried to give 0.52 g of 3-guanidinocarbonyl-1-(quinol-6-yl)-1H-indole hydrochloride in the form of a yellow solid melting at 268° C. IR spectrum (KBr): 3343, 3168, 2174, 1693, 1597, 1543, 1502, 1454, 1236, 1199, 772 and 751 cm−1.

Workup

  1. additionis added
  2. filtrationthe reaction mixture is filtered under an argon atmosphere
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  4. customto give a residue which
  5. additionis subsequently added at 22° C. under an argon atmosphere
  6. stirringAfter stirring at 22° C. for 48 hours and after 2 hours
  7. temperatureat reflux
  8. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  9. customto give a residue which
  10. customis triturated in 15 cm3 of water
  11. stirringAfter stirring at 22° C. for 1 hour
  12. additiona few drops of 10N hydrochloric acid solution are added
  13. stirringAfter stirring at 22° C. for 12 hours
  14. filtrationthe suspension is filtered
  15. customdried

Sources & evidence

ORD record
ord-eae3dd1b67324e69bf3d023c05386695
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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