Hydrochloric Acid → HCID 68992044, compound

HRID 656854Notes

Reaction equation

HRID 656854 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:40])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:41]>C(Cl)(Cl)Cl.O1CCOCC1>[ClH:41].[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:40])[CH2:24][CH2:25]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86635310HCID 86635310, compound

Product 1

HCID 68992044HCID 68992044, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)(1-{2-[7-(methyloxy)-2-oxo-1(2H)-quinolinyl]ethyl}-4-piperidinyl)carbamate (92 mg) in chloroform (1.5 ml) was added 4N HCl in 1,4-dioxane (1.5 ml) and the reaction stirred at rt for 1 h. More 4N HCl in 1,4-dioxane (0.5 ml) was added and the reaction stirred at rt for 0.5 h then the solvents removed. The residue was dissolved in MeOH (25 ml) and treated with Amberlyst A21 basic resin until the pH was 6. The residue was filtered off and the solvent removed; the residue was subjected to column chromatography on silica gel eluting with 0-20% methanol-DCM to afford the free base of the title compound (67 mg, 89%).

Workup

  1. stirringthe reaction stirred at rt for 0.5 h
  2. customthe solvents removed
  3. dissolutionThe residue was dissolved in MeOH (25 ml)
  4. additiontreated with Amberlyst A21 basic resin until the pH was 6
  5. filtrationThe residue was filtered off
  6. customthe solvent removed

Sources & evidence

ORD record
ord-075e627c0c5d49deafd62383bb96e99f
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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