Guanidine → HCID 178464068, compound

HRID 1359616Notes

Reaction equation

HRID 1359616 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:13]([N:15]([CH2:32][CH3:33])[CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29](O)=[O:30])=[CH:24][CH:23]=[CH:22]2)[CH3:14].[NH2:34][C:35]([NH2:37])=[NH:36]>C1COCC1>[CH2:13]([N:15]([CH2:32][CH3:33])[CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([NH:36][C:35]([NH2:37])=[NH:34])=[O:30])=[CH:24][CH:23]=[CH:22]2)[CH3:14]

Participants

5

Reactant 3

HCID 3520GuanidineHCID 682631,1'-CarbonyldiimidazoleHCID 15388932HCID 15388932, compound

Product 1

HCID 178464068HCID 178464068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of CDI are added to a suspension of 2.0 g of 6-(2-diethylaminoethoxy)-1-naphthoic acid in 50 ml of THF, and the reaction mixture is stirred at RT overnight. It is then treated with 2.0 g of guanidine, again stirred overnight and concentrated, and the residue is stirred with 100 ml of water. The precipitate formed is filtered off with suction and purified by FC using methylene chloride/methanol 1:1.0.66 g of 6-(2-diethylaminoethoxy)-1-naphthoylguanidine is obtained; m.p.: 168-169° C. 1H-NMR (DMSO-d6): δ [ppm]=1.0 (6H), 2.6 (4H), 2.85 (2H), 4.15 (2H), 7.15 (1H), 7.3 (1H), 7.4 (1H), 7.75 (2H), 8.7 (1H).

Workup

  1. concentrationconcentrated
  2. stirringthe residue is stirred with 100 ml of water
  3. customThe precipitate formed
  4. filtrationis filtered off with suction
  5. custompurified by FC
  6. customis obtained

Sources & evidence

ORD record
ord-afe7abf3d44b4bfe9fe7c63c02f3f4e6
Source dataset
uspto-grants-2003_07
Patent number
US06600072B2

Reaction notes

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