Guanidine Hydrochloride → HCID 178430100, compound

HRID 1792806Notes

Reaction equation

HRID 1792806 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].[Cl:9][C:10]([C:12]1[C:16]([CH3:17])=[CH:15][N:14]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]=2)[CH:13]=1)=[O:11]>COCCOC.C(Cl)(Cl)Cl.CO>[ClH:9].[NH:7]([C:10]([C:12]1[C:16]([CH3:17])=[CH:15][N:14]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]=2)[CH:13]=1)=[O:11])[C:6]([NH2:8])=[NH:5]

Participants

7

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 220249491-(Isoquinolin-1-yl)-4-methyl-1H-pyrrole-3-carbonyl chloride

Product 1

HCID 178430100HCID 178430100, compoundYield 43.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

1.37 g (25.37 mmol) of sodium methoxide are added at a temperature in the region of 20° C. under an argon atmosphere to 25 mL of methanol. After complete dissolution, 2.5 g (26.2 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° 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 25 mL of 1,2-dimethoxyethane and then again concentrated to dryness. The residue is suspended in a mixture of 50 mL of tetrahydrofuran, 25 mL of acetonitrile and 50 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere and then 1.18 g (4.36 mmol) of 3-chlorocarbonyl-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole, dissolved in 20 mL of chloroform, are added thereto. After stirring at a temperature in the region of 20° C. 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 mL of water. After filtering, a gum is obtained, which gum is dissolved in 50 mL of methanol. The solution obtained is partially concentrated to a volume of 5 to 10 mL and is then purified by silica gel chromatography [eluent: chloroform/methanol (75/25 by volume)]. After concentrating the fractions under reduced pressure and triturating in ethyl ether, 0.62 g of 3-guanidinocarbonyl-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole hydrochloride is obtained in the form of a white solid melting at 247° C. Mass spectrum (EI): EI: m/e 293 (M+.), m/e 234.

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. concentrationagain concentrated to dryness
  5. additionThe residue is suspended in a mixture of 50 mL of tetrahydrofuran, 25 mL of acetonitrile and 50 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere
  6. additionare added
  7. stirringAfter stirring at a temperature in the region of 20° C. for 18 hours
  8. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  9. customto give a residue which
  10. customis triturated in 100 mL of water
  11. filtrationAfter filtering
  12. customa gum is obtained
  13. customThe solution obtained
  14. concentrationis partially concentrated to a volume of 5 to 10 mL
  15. customis then purified by silica gel chromatography [eluent: chloroform/methanol (75/25 by volume)]
  16. concentrationAfter concentrating the fractions under reduced pressure
  17. customtriturating in ethyl ether

Sources & evidence

ORD record
ord-ec81f6d9662f4a75babd0b2c6e4714da
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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