Sulfuric Acid → HCID 86712594, compound

HRID 2175279Notes

Reaction equation

HRID 2175279 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][CH2:15][N:16]3[C:21](=[O:34])[CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:27]=2[CH3:33])[CH:8]=[N:7]1.OS(O)(=O)=O>CC(C)=O>[CH3:33][C:27]1[C:28]([CH3:32])=[CH:29][CH:30]=[CH:31][C:26]=1[O:25][CH2:24][CH2:23][CH2:22][C:21]([N:16]1[C:17]2[C:12](=[C:11]([C:9]3[CH:8]=[N:7][N:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH:10]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:14][CH2:15]1)=[O:34]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86712595HCID 86712595, compound

Product 1

HCID 86712594HCID 86712594, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(5-(1-(3,3-dimethoxypropyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one (40 mg, 0.081 mmol) in acetone (0.8 mL) was added 9 M H2SO4. The reaction mixture was stirred at room temperature for 2 h. After this time, the reaction mixture was partitioned between DCM and saturated NaHCO3, and stirred for 15 min. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound (36 mg, 100% yield). 1H NMR (400 MHz, CDCl3) δ 9.86 (s, 1H), 7.50 (s, 1H), 7.38 (s, 1H), 7.21-7.12 (m, 2H), 7.02 (t, J=7.9 Hz, 1H), 6.75 (d, J=7.5 Hz, 1H), 6.65 (d, J=8.1 Hz, 1H), 6.09 (s, 1H), 4.48 (t, J=6.3 Hz, 2H), 3.94 (s, 2H), 3.81-3.75 (m, 2H), 3.14 (t, J=6.3 Hz, 2H), 2.74 (t, J=7.1 Hz, 2H), 2.63 (s, 2H), 2.59 (d, J=4.3 Hz, 2H), 2.14 (s, 3H), 1.95-1.81 (m, 5H).

Workup

  1. customAfter this time, the reaction mixture was partitioned between DCM and saturated NaHCO3
  2. stirringstirred for 15 min
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-74e3fee73f084675afcc37fdfa1e30b1
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…