Guanidine Hydrochloride → HCID 178479501, compound

HRID 1869151Notes

Reaction equation

HRID 1869151 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].O1CCCC1.Cl.[Cl:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[CH:19]=1)=[O:17]>CO.ClCCl>[ClH:15].[NH:7]([C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=[C:29]([C:37]([F:39])([F:38])[F:40])[CH:28]=2)[CH:19]=1)=[O:17])[C:6]([NH2:8])=[NH:5]

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 865947943-chlorocarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride

Product 1

HCID 178479501HCID 178479501, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

20 cm3 of methanol and 8.4 cm3 (4.2 mmol) of a 0.5N solution of sodium methoxide in methanol are added to 0.401 g (4.2 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 and 0.35 g (0.85 mmol) of 3-chlorocarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride, suspended in 20 cm3 of dichloromethane, are then 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 solid obtained is triturated in 20 cm3 of isopropyl ether and filtered off, resulting in 0.1 g of 3-guanidinocarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride in the form of a white powder melting at 216° 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 then 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 solid obtained
  11. customis triturated in 20 cm3 of isopropyl ether
  12. filtrationfiltered off

Sources & evidence

ORD record
ord-23f69fcde7464b2e80459812699351af
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

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