Hydrochloric Acid → HCID 86722490, compound

HRID 718876Notes

Reaction equation

HRID 718876 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N: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][C@H: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>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N: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:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86722489HCID 86722489, compound

Product 1

HCID 86722490HCID 86722490, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

rac-(4aR,13bS)-9-(4-Fluorophenyl)-13 b-(pyridin-2-ylmethyl)-1,2,4,4a,5,6,7,13 b-octahydrospiro[benzo[3,4]cyclohepta[1,2-d][1,2,3]triazolo[1,5-a]pyridine-3,2′-[1,3]dioxolane] (156, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.230 g, 0.475 mmol) in acetone (3 mL) was treated with 6 N hydrochloric acid (0.060 mL, 0.322 mmol) then stirred at rt for about 3 h. Sat. aq. NaHCO3 (˜5 mL) and EtOAc (15 mL) were added to the mixture then the layers were separated. The organic layer was washed with brine (˜5 mL) then dried over MgSO4, filtered and concentrated in vacuo 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][1,2,3]triazolo[1,5-a]pyridin-3(2H)-one (157, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.142 g, 68%); LC/MS, method 3, Rt=2.30 min, MS m/z 441 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.40 (s, 1H), 8.36-8.27 (m, 1H), 8.12 (s, 1H), 8.11-8.03 (m, 2H), 7.48-7.30 (m, 3H), 7.08-6.98 (m, 1H), 6.64 (d, J=7.8 Hz, 1H), 3.85-3.73 (m, 1H), 3.55-3.42 (m, 2H), 2.75-2.64 (m, 1H), 2.42-2.23 (m, 3H), 2.20-2.02 (m, 5H), 1.79-1.68 (m, 1H), 1.49-1.36 (m, 1H), 1.29-1.21 (m, 1H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine (˜5 mL)
  3. dry with materialthen dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c548851c40148e69ce5b0f49a65c6d5
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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