4-Chlorobenzylamine → HCID 178522927, compound

HRID 2086598Notes

Reaction equation

HRID 2086598 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([I:19])[CH:8]=[C:9]([CH2:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:20](OCC)=[O:21].[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:20]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([CH2:12][CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:8][C:7]=3[I:19])=[O:21])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469654HCID 178469654, compound

Product 1

HCID 178522927HCID 178522927, compoundYield 75%

Conditions

Temperature
180 °C

Procedure

A suspension of ethyl 4-hydroxy-8-iodo-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxylate (0.8 g) and 4-chlorobenzylamine (1.54 mL) is heated to 180° C. for 1 h. The reaction is cooled to room temperature. The resulting solid is collected and washed with Et2O. The crude solid is adsorbed onto silica and chromatographed (Biotage flash 40S, eluent 1% MeOH/CH2Cl2 then 2% MeOH/CH2Cl2). Fractions homogeneous by TLC are combined and concentrated. The resulting solid is triturated with EtOAc/hexanes to yield 0.73 g (75%) of the desired product as a white solid.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customThe resulting solid is collected
  3. washwashed with Et2O
  4. customchromatographed (Biotage flash 40S, eluent 1% MeOH/CH2Cl2
  5. concentrationconcentrated
  6. customThe resulting solid is triturated with EtOAc/hexanes

Sources & evidence

ORD record
ord-30884896f53046b7bf20f94880fb6228
Source dataset
uspto-grants-2004_04
Patent number
US06727248B2

Reaction notes

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