Guanidine Hydrochloride → HCID 178479504, compound

HRID 1869163Notes

Reaction equation

HRID 1869163 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](=[C:32]([C:37]([F:40])([F:39])[F:38])[CH:33]=[CH:34][CH:35]=3)[N:30]=[CH:29][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](=[C:32]([C:37]([F:39])([F:38])[F:40])[CH:33]=[CH:34][CH:35]=3)[N:30]=[CH:29][CH:28]=2)[CH:19]=1)=[O:17])[C:6]([NH2:8])=[NH:5]

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 86594800HCID 86594800, compound

Product 1

HCID 178479504HCID 178479504, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

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 evaporated to dryness under reduced pressure (2.7 kPa). 30 cm3 of tetrahydrofuran and 0.525 g (1.4 mmol) of 3-chlorocarbonyl-1-(8-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride, suspended in 30 cm3 of dichloromethane, 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 diisopropyl ether and filtered off, resulting in 0.14 g of 3-guanidinocarbonyl-1-(8-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride in the form of a white powder melting at 212° 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. customevaporated 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 diisopropyl ether
  12. filtrationfiltered off

Sources & evidence

ORD record
ord-078bea8ce5214d7eb900d2ac87bd0643
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

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