Hydrochloric Acid → HCID 68154067, compound

HRID 341087Notes

Reaction equation

HRID 341087 reaction equation
[O:1]=[C:2]1[C:6]2=[CH:7][N:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[CH2:27][C:28]([O:30]CC)=[O:29].[OH-].[Li+].Cl>O1CCOCC1.ClCCl>[O:1]=[C:2]1[C:6]2=[CH:7][N:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[CH2:27][C:28]([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 131732098HCID 131732098, compound

Product 1

HCID 68154067HCID 68154067, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl (3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazol[4,3-c]quinolin-2-yl)acetate (Example 524, 10 mg, 0.023 mmol) was suspended in dioxane (2 mL), treated with an lithium hydroxide (22 μL, 1 N aqueous, 0.023 mmol, 1.05 equiv) and stirred vigorously for 18 hours. The mixture was diluted with dichloromethane until homogeneous (2 mL) and stirred for an additional 6 hours. The mixture was treated with hydrochloric acid (1 drop from 9″ pipette, 12 N aqueous) and concentrated in vacuo, providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.06 (1H, s), 8.44 (1H, d, J=2.7 Hz), 8.15 (1H, d, J=7.9 Hz), 7.81 (2H, d, J=8.8 Hz), 7.74 (1H, d, J=8.5 Hz), 7.71 (1H, d, J=1.3 Hz), 7.58 (1H, t, 7.8 Hz), 7.50 (1H, t, J=7.3 Hz), 7.43 (2H, d, J=8.5 Hz), 7.14 (1H, hr s), 6.52 (1H, m), 5.74 (2H, s), 4.59 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 400.1412 [(M+H)+; calculated for C22H18N5O3: 400.1404].

Workup

  1. stirringstirred for an additional 6 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fb01dafd94c4462b3827b8bf612e50a
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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