HCID 13237005, compound → HCID 86702430, compound

HRID 2278447Notes

Reaction equation

HRID 2278447 reaction equation
CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:5]([C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])=O.[ClH:20].[N:21]1([C:28](=[NH:30])[NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CC(C)([O-])C.[K+]>C(O)C.O>[ClH:20].[CH3:12][C:8]1[O:9][CH:10]=[CH:11][C:7]=1[C:5]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:3][N:29]=[C:28]([N:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:30]=1

Participants

6

Reactant 3

HCID 13237005HCID 13237005, compoundHCID 23665647Potassium tert-butoxideHCID 67514434HCID 67514434, compound

Product 1

HCID 86702430HCID 86702430, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(2-methyl-3-furanyl)-2-(2-pyridinyl)-2-propen-1-one (205 mg, 0.8 mmol) and hexahydro-1H-azepine-1-carboximidamide hydrochloride (213 mg, 1.200 mmol) in ethanol (4 ml) was stirred at room temperature. Potassium tert-butoxide (180 mg, 1.600 mmol) was added and the mixture was heated at reflux for 45 minutes. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC. The product was dissolved in a mixture of dichloromethane (2 ml) and methanol (0.5 ml) and hydrogen chloride (1M in ether, 0.5 ml) was added and the solvent was evaporated. The residue was co-evaporated with ether and triturated with ether. The solid was collected and dried to give the title compound (67 mg, 23%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.74 (2H, d), 8.54 (1H, s), 8.12-8.10 (1H, m), 7.65-7.55 (2H, m), 7.43 (1H, d), 5.74 (1H, d), 3.84-3.80 (4H, m), 2.41 (3H, s), 1.85-1.70 (4H, m), 1.60-1.48 (4H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. extractionextracted with ethyl acetate
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified
  9. dissolutionThe product was dissolved in a mixture of dichloromethane (2 ml) and methanol (0.5 ml) and hydrogen chloride (1M in ether, 0.5 ml)
  10. additionwas added
  11. customthe solvent was evaporated
  12. customtriturated with ether
  13. customThe solid was collected
  14. customdried

Sources & evidence

ORD record
ord-7c2a5a78c4da4c1a8a528cfa697eb1be
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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