Ammonia → HCID 86757913, compound

HRID 840112Notes

Reaction equation

HRID 840112 reaction equation
[N:1]1([CH2:14][C@@H:15]([NH2:17])[CH3:16])[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[CH:3]=[CH:2]1)[N:10]=[CH:9][CH:8]=[CH:7]3.[CH2:18]1[O:28][C:27]2[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=2[O:19]1.[BH4-].C(=O)C1C=CC=CC=1.N.[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43]>CC(O)C.CO>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[N:1]1([CH2:14][C@@H:15]([NH:17][CH2:23][C:22]2[CH:25]=[CH:26][C:27]3[O:28][CH2:18][O:19][C:20]=3[CH:21]=2)[CH3:16])[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[CH:3]=[CH:2]1)[N:10]=[CH:9][CH:8]=[CH:7]3

Participants

9

Reactant 6

HCID 222AmmoniaHCID 240BenzaldehydeHCID 8438PiperonalHCID 28123BorohydrideHCID 444972Fumaric AcidHCID 10198431HCID 10198431, compound

Product 1

HCID 86757913HCID 86757913, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (S)-1-(1H-pyrrolo[2,3-f]quinolin-1-yl)-2-propylamine (0.025 g, 0.11 mmol), 3,4-methylenedioxybenzaldehyde (0.033 g, 0.22 mmol) and methanol (1 mL) was shaken for 3 h. To the mixture was added Amberlite IRA-400 borohydride resin (2.5 mmol/g —BH4, 0.12 g, 0.3 mmol) and the mixture was shaken for 18 h. To the mixture was added PS-benzaldehyde (2.5 mmol/g —CHO, 0.12 g, 0.3 mmol) and the mixture was shaken for 18 h and filtered. The filter-cake was washed with dichloromethane (2×1 mL) and methanol (2×1 mL) and the filtrate was concentrated in vacuo. The concentrate was dissolved in dichloromethane (2 mL) and Amberlyst-15 (0.5 g) was added. The mixture was shaken for 1 h and filtered. The filter-cake was washed with dichloromethane (2×1 mL) and methanol (2×1 mL), suspended in methanolic ammonia solution (2 M, 1 ML, 2 mmol), shaken for 1 h, and filtered. The filter-cake was washed (dichloromethane) and the filtrate was concentrated in vacuo, treated with a solution of fumaric acid (0.030 g, 0.26 mmol) in 2-propanol (2 mL), cooled to 0° C., shaken for 1 h and filtered. The filter-cake was dried to give the product as a beige solid (0.052 g, 79%): mp 171-175° C. (dec); NMR ΔH (400 MHz, DMSO-d6) 0.99 (3H, d, J 6.5 Hz) 3.15 (1H, m) 3.58 (1H, d, J 14 Hz) 3.73 (1H, d, J 14 Hz) 4.46 (1H, dd, J 8.5, 14.5 Hz) 4.76 (1H, dd, J 6, 14.5 Hz) 5.96 (2H, s) 6.66 (1H, d, J 7.5 Hz) 6.73 (1H, d, J 7.5 Hz) 6.87 (1H, s) 7.47 (1H, dd, J 4.5, 8.5 Hz) 7.50 (1H, d, J 3 Hz) 7.64 (1H, d, J 9 Hz) 7.94 (1H, d, J 9 Hz) 8.64 (1H, d, J 8.5 Hz) 8.77 (1H, d, J 4 Hz).

Workup

  1. stirringthe mixture was shaken for 18 h
  2. stirringthe mixture was shaken for 18 h
  3. filtrationfiltered
  4. washThe filter-cake was washed with dichloromethane (2×1 mL) and methanol (2×1 mL)
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe concentrate was dissolved in dichloromethane (2 mL)
  7. additionAmberlyst-15 (0.5 g) was added
  8. stirringThe mixture was shaken for 1 h
  9. filtrationfiltered
  10. washThe filter-cake was washed with dichloromethane (2×1 mL) and methanol (2×1 mL)
  11. stirringshaken for 1 h
  12. filtrationfiltered
  13. washThe filter-cake was washed (dichloromethane)
  14. concentrationthe filtrate was concentrated in vacuo
  15. stirringshaken for 1 h
  16. filtrationfiltered
  17. customThe filter-cake was dried

Sources & evidence

ORD record
ord-579215b2f5444066a5c3cf55264c9ad1
Source dataset
uspto-grants-2002_04
Patent number
US06365598B1

Reaction notes

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