Hydrochloric Acid → HCID 46837056, compound

HRID 1518416Notes

Reaction equation

HRID 1518416 reaction equation
Cl.Cl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][NH:22][CH2:21][CH2:20]2)=[O:14].[OH2:25].Cl.[CH3:27][CH2:28][OH:29]>>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][N:22]([C:6]1[N:5]=[C:27]([C:28]([OH:25])=[O:29])[CH:9]=[CH:8][CH:7]=1)[CH2:21][CH2:20]2)=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

Product 1

HCID 46837056HCID 46837056, compoundYield 67%

Procedure

Compound 1B (71 mg, 0.15 mmol) was dissolved in 2 mL of EtOH. Two milliliters of water were then added followed by 2 mL of concentrated HCl. The reaction was stirred at room temperature for 72 hours until LCMS indicated complete conversion. Nitrogen gas was bubbled through the mixture to remove HCl and EtOH; a white solid precipitated. It was collected by filtration, rinsed with water and a small amount of Et2O and dried under vacuum to provide the product as a white solid (42 mg, 67%): 1HNMR (ppm, DMSO) 2.98 (t, J=6.15 Hz, 2H), 3.92 (t, J=6.06 Hz, 2H), 4.95 (s, 2H), 7.02 (d, J=8.5 Hz, 1H), 7.27 (d, J=7.3 Hz, 7.31-7.49 (m, 4H), 758 (d, J=7.5 Hz, 1H), 7.66-7.71 (m, 1H), 7.77 (d, J=8.0 Hz, 1H), 8.02 (d, J=7.9 Hz); LCMS m/z 431.0 (M+1).

Workup

  1. customNitrogen gas was bubbled through the mixture
  2. customto remove HCl and EtOH
  3. customa white solid precipitated
  4. filtrationIt was collected by filtration
  5. washrinsed with water
  6. dry with materiala small amount of Et2O and dried under vacuum

Sources & evidence

ORD record
ord-6fbc9250550646c484ec6a8194aaac8b
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…