Diisopropylethylamine → HCID 22348261, compound

HRID 897230Notes

Reaction equation

HRID 897230 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[C:6]2[NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C.[CH2:31]1[O:41][C:40]2[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][C:33]=2[O:32]1>CN(C=O)C.C(Cl)Cl>[O:41]1[C:40]2[CH:39]=[CH:38][C:35]([CH2:36][N:19]3[CH2:20][CH2:21][CH:16]([NH:15][C:6]4[C:5]5[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=4)[CH2:17][CH2:18]3)=[CH:34][C:33]=2[O:32][CH2:31]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 223480146-Methoxy-1-methyl-4-(piperidin-4-ylamino)-1H-quinolin-2-one

Product 1

HCID 22348261HCID 22348261, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-methoxy-1-methyl-4-(piperidin-4-ylamino)-1H-quinolin-2-one (300 mg, 0.8 mmol) and diisopropylethlyamine (705 uL, 4 mmol) in DMF (5 mL) was added a solution of 3,4 methylenedioxybenzyl chloride in methylene chloride (231 uL, 0.9 mmol, 50% by weight in CH2Cl2). After stirring at room temperature for 2 hours, the reaction mixture was diluted up with methylene chloride, washed with brine and dried with MgSO4. The residue was purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v) to provide the title compound (66.4 mg, 20%): 1H NMR (300 MHz, CDCl3) δ 1.58-1.72 (2H, m), 2.10-2.23 (4H, m), 2.88-2.98 (2H, m), 3.40-3.50 (1H, m), 3.48 (3H, s), 3.64 (3H, s), 4.58 (1H, bd, J=7.5), 5.75 (1H, s), 5.95 (2H, s), 6.77 (2H, s), 6.89 (1H, s), 7.25 (1H, d; J=1.89 Hz), 7.26 (1H, s), 7.40 (1H, dd, j=1.79, 8.75 Hz).

Workup

  1. washwashed with brine
  2. dry with materialdried with MgSO4
  3. customThe residue was purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v)

Sources & evidence

ORD record
ord-4d5e4eadd29b4f239ec7135882531d8d
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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