Hydrochloric Acid → HCID 86722482, compound

HRID 718866Notes

Reaction equation

HRID 718866 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[CH:16]=[C:15]4[C:17]5([CH2:30][C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=6)[CH2:29][CH2:28][C:23]6(OCC[O:24]6)[CH2:22][CH:18]5[CH2:19][CH2:20][CH2:21][C:14]4=[CH:13][C:12]=23)=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[CH:16]=[C:15]4[C:17]5([CH2:30][C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=6)[CH2:29][CH2:28][C:23](=[O:24])[CH2:22][CH:18]5[CH2:19][CH2:20][CH2:21][C:14]4=[CH:13][C:12]=23)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86722483HCID 86722483, compound

Product 1

HCID 86722482HCID 86722482, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

rac-(4aR,13bS)-9-(4-Fluorophenyl)-13b-(pyridin-2-ylmethyl)-1,2,4,4a,5,6,7,13b-octahydro spiro[benzo[3,4]cyclohepta[1,2-d]imidazo[1,5-a]pyridine-3,2′-[1,3]dioxolane] (148, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.380 g, 0.786 mmol) in 1,4-dioxane (8 mL) and water (2 mL) was treated with 6 N hydrochloric acid (0.52 mL, 3.1 mmol) then stirred at rt for about 4 h. Water (1 mL) was added and the mixture was stirred for about 12 h. Sat. aq. NaHCO3 (˜10 mL) and EtOAc (20 mL) were added to the mixture then the layers were separated. The organic layer was washed with brine (˜15 mL) then dried over MgSO4, filtered and concentrated to yield rac-(4aR,13bS)-9-(4-fluorophenyl)-13b-(pyridin-2-ylmethyl)-4,4a,5,6,7,13b-hexahydro-1H-benzo[3,4]cyclohepta[1,2-d]imidazo[1,5-a]pyridin-3(2H)-one (149, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.323 g, 94%); LC/MS, method 3, Rt=2.30 min, MS m/z 440 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.38-8.36 (m, 1H), 8.18 (s, 1H), 7.96-7.90 (m, 3H), 7.75 (s, 1H), 7.43-7.39 (m, 1H), 7.27-7.19 (m, 2H), 7.08-7.04 (m, 1H), 6.59 (d, J=7.8 Hz, 1H), 3.70 (d, J=13.6 Hz, 1H), 3.45-3.38 (m, 2H), 3.20-3.02 (m, 2H), 2.69-2.62 (m, 1H), 2.29-1.87 (m, 7H), 1.72-1.63 (m, 1H), 1.46-1.32 (m, 1H).

Workup

  1. stirringthe mixture was stirred for about 12 h
  2. customthe layers were separated
  3. washThe organic layer was washed with brine (˜15 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2125b56adda748aaaf50fad44a4cdcfb
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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