1,2-Dichloroethane → HCID 86732731, compound

HRID 525864Notes

Reaction equation

HRID 525864 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]([OH:22])=O)[CH:16]=3)[N:11]([CH3:23])[CH:10]=2)=[CH:5][CH:4]=1.[N:26]1([CH2:31][CH2:32][NH2:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]([NH:33][CH2:32][CH2:31][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[O:22])[CH:16]=3)[N:11]([CH3:23])[CH:10]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 181649HOAtHCID 86732727HCID 86732727, compound

Product 1

HCID 86732731HCID 86732731, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a suspension of 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (Example 5e) (0.588 g, 1.733 mmol), 2-(pyrrolidin-1-yl)ethanamine (0.240 ml, 1.906 mmol), EDC (0.3865 g, 2.016 mmol), HOAt (0.1218 g, 0.895 mmol) in dichloromethane (16 ml) was added triethylamine (1.7 ml, 12.20 mmol), and the mixture was allowed to stir at 30° C. for 24 h. After cooling, the reaction was concentrated and the residue was purified on a silica gel column (24 g), eluting with 0-20% methanol/dichloroethane (2% ammonium hydroxide). The desired fractions were collected, concentrated. The solid was washed with water, filtered, and dried in vacuo to afford 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydroquinoline-6-carboxamide (0.595 g, 1.366 mmol, 79% yield) as white solid. LCMS: (M+H)+: 436.2.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction was concentrated
  3. customthe residue was purified on a silica gel column (24 g)
  4. washeluting with 0-20% methanol/dichloroethane (2% ammonium hydroxide)
  5. customThe desired fractions were collected
  6. concentrationconcentrated
  7. washThe solid was washed with water
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a9a71e071ee74faab2dad9577f3587c7
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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