Guanidine Hydrochloride → GW-2580

HRID 1725586Notes

Reaction equation

HRID 1725586 reaction equation
[NH:1]([CH:8]=[C:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[C:15]([O:29][CH3:30])[CH:14]=1)[C:10]#N)C1C=CC=CC=1.Cl.[NH2:32][C:33]([NH2:35])=[NH:34].C[O-].[Na+].[OH-].[Na+]>C(O)C.CCCCCC>[CH3:30][O:29][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[CH2:12][C:9]1[C:8]([NH2:1])=[N:34][C:33]([NH2:35])=[N:32][CH:10]=1

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 69006529HCID 69006529, compound

Product 1

HCID 11617559GW-2580Yield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

A suspension of 3-anilino-2-{3-methoxy-4-[(4-methoxybenzyl) oxy]benzyl}prop-2-enenitrile (300 mg, 0.75 mmol) and guanidine hydrochloride (108 mg, 1.13 mmol) in ethanol (5 mL) was stirred at room temperature while sodium methoxide was added. The mixture was stirred at reflux overnight. The solution was cooled 5 C and 2N sodium hydroxide (2 mL) was added. After 15 minutes, a white precipitate was filtered off and washed with water then hexane to give product as a white solid (199 mg, 0.54 mmol). 1H NMR (300 MHz, d6-DMSO): δ 7.45 (s, 1H), 7.32 (d, J=8.6 Hz, 2H), 6.93-6.85 (m, 4H), 6.66 (dd, J=8.3 and 1.5 Hz, 1H), 6.02 (s, 2H), 5.65 (s, 2H), 4.91 (s, 2H), 3.73 (s, 3H), 3.70 (s, 3H), 3.50 (s, 2H). MS (ES+, m/z)=367 (M+H).

Workup

  1. additionwas added
  2. temperatureat reflux overnight
  3. additionwas added
  4. filtrationa white precipitate was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-5feb46a11562457a94a68d6ade16046e
Source dataset
uspto-grants-2009_02
Patent number
US07491731B2

Reaction notes

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