Guanidine Hydrochloride → HCID 178479503, compound

HRID 1869159Notes

Reaction equation

HRID 1869159 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].[Cl:9]CCl.Cl.Cl[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C:25]2[C:34]3[C:29](=[CH:30][C:31]([C:35]([F:38])([F:37])[F:36])=[CH:32][CH:33]=3)[N:28]=[CH:27][CH:26]=2)[CH:17]=1)=[O:15]>CO.O1CCCC1>[ClH:9].[NH:7]([C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C:25]2[C:34]3[C:29](=[CH:30][C:31]([C:35]([F:37])([F:36])[F:38])=[CH:32][CH:33]=3)[N:28]=[CH:27][CH:26]=2)[CH:17]=1)=[O:15])[C:6]([NH2:8])=[NH:5]

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 865947983-chlorocarbonyl-1-(7-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride

Product 1

HCID 178479503HCID 178479503, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

20 cm3 of methanol and 14 cm3 (7 mmol) of a 0.5M solution of sodium methoxide in methanol are added to 0.67 g (7 mmol) of guanidine hydrochloride under an argon atmosphere. After stirring at a temperature in the region of 25° C. for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is three times successively dissolved in 20 cm3 of dichloromethane and concentrated to dryness under reduced pressure (2.7 kPa). 40 cm3 of tetrahydrofuran, 40 cm3 of dichloromethane and 0.525 g (1.4 mmol) of 3-chlorocarbonyl-1-(7-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride, suspended in 20 cm3 of tetrahydrofuran, are subsequently added thereto under an argon atmosphere. After stirring at a temperature in the region of 20° C. for 16 hours, the reaction mixture is concentrated to give a solid which is purified by flash chromatography [eluent: ethyl acetate/methanol (9/1 and then 8/2 by volume)]. After concentrating the fractions to dryness under reduced pressure (2.7 kPa), the product obtained is triturated in 20 cm3 of isopropyl ether and filtered off, resulting in 0.1 g of 3-guanidinocarbonyl-1-(7-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride in the form of a white powder melting at 238° C. Mass spectrum (EI): m/e 397 (M+•), m/e 339 (base peak).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. dissolutionsuccessively dissolved in 20 cm3 of dichloromethane
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. additionare subsequently added
  5. stirringAfter stirring at a temperature in the region of 20° C. for 16 hours
  6. concentrationthe reaction mixture is concentrated
  7. customto give a solid which
  8. customis purified by flash chromatography [eluent
  9. concentrationAfter concentrating the fractions to dryness under reduced pressure (2.7 kPa)
  10. customthe product obtained
  11. customis triturated in 20 cm3 of isopropyl ether
  12. filtrationfiltered off

Sources & evidence

ORD record
ord-b6f7d41c76da4690869a3ec8175aa955
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

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