Iodoethane → 5-Ethyl-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752621Notes

Reaction equation

HRID 1752621 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[N:10]1([C:16]2[C:21](=[O:22])[NH:20][CH:19]=[C:18]3[CH2:23][N:24]([CH2:27][CH2:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[C:25](=[O:26])[C:17]=23)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>C(#N)C.O>[CH2:8]([N:20]1[C:21](=[O:22])[C:16]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:17]2[C:25](=[O:26])[N:24]([CH2:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH2:23][C:18]2=[CH:19]1)[CH3:9]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 862960597-Morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

Product 1

HCID 862960605-Ethyl-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 35.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (2.5 g, 18.09 mmol), iodoethane (0.103 ml, 1.281 mmol) and 7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (0.5 g, 1.281 mmol, see Example 15) were suspended in acetonitrile (30 ml). The suspension was heated in a three-neck round bottom flask at about 60° C. for about 2 h. After cooling to r.t. LC-MS analysis indicated complete conversion. The reaction mixture was diluted with water. The aqueous layer was extracted with DCM (2×100 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to give a yellow solid which was purified by preparative HPLC to give the title compound (190 mg, 0.454 mmol, 35.5 yield) as a yellow solid.

Workup

  1. temperatureAfter cooling to r.t
  2. extractionThe aqueous layer was extracted with DCM (2×100 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow solid which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-fb2a8afcd6b24d469b313ca45a43eb22
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

Loading…