Guanidine Hydrochloride → HCID 10200445, compound

HRID 2415111Notes

Reaction equation

HRID 2415111 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:24][CH3:25])[CH:8]=[C:9]([CH2:12][C:13](=[CH:16]NC3C=CC=CC=3)[C:14]#[N:15])[CH:10]=2)[O:5][C:4]([CH3:27])([CH3:26])[CH:3]=1.Cl.[NH2:29][C:30]([NH2:32])=[NH:31].CC(C)([O-])C.[K+]>C(O)C>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:24][CH3:25])[CH:8]=[C:9]([CH2:12][C:13]3[C:14]([NH2:15])=[N:31][C:30]([NH2:32])=[N:29][CH:16]=3)[CH:10]=2)[O:5][C:4]([CH3:27])([CH3:26])[CH:3]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 69898773HCID 69898773, compound

Product 1

HCID 10200445HCID 10200445, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above prepared 418 mg of 2-(4-bromo-8-methoxy-2,2-dimethyl-2H-chromen-6-ylmethyl)-3-phenylamino-acrylonitrile were treated with 248 mg of guanidine hydrochloride (3.3 eq.), 291 mg of potassium-t-butoxide (3.3 eq.) and 16 ml of ethanol and heated under reflux under argon atmosphere for 14 hours. After cooling, the reaction mixture was poured onto crushed ice, extracted twice with AcOEt, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2 with CH2Cl2/MeOH/25% NH3=19/1/0.05), followed by crystallization from EtOEt afforded 186 mg of the title compound as light-yellow crystals, mp.238-239°.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon atmosphere for 14 hours
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured
  5. customonto crushed ice
  6. extractionextracted twice with AcOEt
  7. washwashed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. customFlash chromatography (SiO2 with CH2Cl2/MeOH/25% NH3=19/1/0.05), followed by crystallization from EtOEt

Sources & evidence

ORD record
ord-c54654863e464979ba5e29ba4c012c42
Source dataset
uspto-grants-2004_11
Patent number
US06818649B2

Reaction notes

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