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Guanidine Hydrochloride → HCID 178513072, compound

HRID 492213
Notes
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Reaction equation

HRID 492213 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].Cl.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]1[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][CH:21]=1)[CH:15]=[C:14]2[C:30](Cl)=[O:31].[K+].[Br-]>CO>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]1[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][CH:21]=1)[CH:15]=[C:14]2[C:30]([NH:4][C:3]([NH2:5])=[NH:2])=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 253877Potassium BromideHCID 10942334Sodium MethoxideHCID 86596417HCID 86596417, compound

Product 1

HCID 178513072HCID 178513072, compound

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

3.11 g (32.55 mmol) of guanidine hydrochloride are added to a solution of 1.76 g (32.55 mmol) of sodium methoxide in 60 cm3 of methanol at a temperature in the region of 20° C. under an argon atmosphere. After stirring at this temperature for 2 hours, the mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 60 cm3 of 1,2-dimethoxyethane, and 2.46 g (6.51 mmol) of 5-chloro-3-chlorocarbonyl-1-(quinolin-4-yl)-1H-indole hydrochloride are added. After stirring at the reflux temperature of the solvent for 2 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is triturated in 250 cm3 of water and the suspension is filtered and then dried. The residue is purified by chromatography on silica gel [eluent: dichloromethane/methanol (85/15 by volume)]. After the fractions containing the expected product have been concentrated to dryness under reduced pressure (2.7 kPa), 1.2 g of 5-chloro-3-guanidinocarbonyl-1-(quinolin-4-yl)-1H-indole are obtained in the form of a beige-colored powder melting at a temperature above 260° C. Mass spectrum (CI): m/e 363 (M+H)+)+ (base peak). IR spectrum (KBr): 3466; 3398; 3322; 1636; 1593; 1571; 1510; 1451; 1383; 1356; 1265; 1219; 881; 810; 792; 775 and 649 cm−1.

Workup

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. stirringAfter stirring at the reflux temperature of the solvent for 2 hours
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is triturated in 250 cm3 of water
  5. filtrationthe suspension is filtered
  6. customdried
  7. customThe residue is purified by chromatography on silica gel [eluent: dichloromethane/methanol (85/15 by volume)]
  8. additionAfter the fractions containing the expected product
  9. concentrationhave been concentrated to dryness under reduced pressure (2.7 kPa), 1.2 g of 5-chloro-3-guanidinocarbonyl-1-(quinolin-4-yl)-1H-indole
  10. customare obtained in the form of a beige-colored powder
  11. custommelting at a temperature above 260° C

Sources & evidence

ORD record
ord-74735bc2dc904a87872b11e888e5e7c0
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531663B2

Reaction notes

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