Guanidine Hydrochloride → HCID 178486745, compound

HRID 228977Notes

Reaction equation

HRID 228977 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([O:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:37][C:38]([NH2:40])=[NH:39].[H-].[Na+]>O.CN(C)C=O>[CH3:29][O:28][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][NH:39][C:38]([NH2:40])=[NH:37])[N:13]=[CH:12][CH:11]=[C:10]2[O:16][C:17]1[C:18]([CH3:27])=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 230785037-(3-Chloro-propoxy)-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline2×

Product 1

HCID 178486745HCID 178486745, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (1 ml) was added to 7-(3-chloro-propoxy)-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (compound 375) (40 mg), potassium carbonate (41 mg), and guanidine hydrochloride (28 mg). Sodium hydride (39 mg) was added to the mixture, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with n-butanol. The n-butanol layer was washed with water and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (7 mg, yield 17%).

Workup

  1. extractionthe mixture was extracted with n-butanol
  2. washThe n-butanol layer was washed with water
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-0aeb4c446e4b458e8d067c1e0b1cde6d
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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