4-Chlorobenzylamine → HCID 178522876, compound

HRID 2289891Notes

Reaction equation

HRID 2289891 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[C:28]([OH:30])=O.[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>O1CCCC1>[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:37][C:28]([C:15]2[CH:16]=[N:17][C:18]3[C:23]([C:14]=2[OH:13])=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=3)=[O:30])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524718HCID 178524718, compound

Product 1

HCID 178522876HCID 178522876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.892 g 1,1'-carbonyldiimidazole in 30 mL of tetrahydrofuran is added 1.29 g 4-hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid. The reaction is stirred at room temperature for 1 h. A solution of 0.91 mL of 4-chlorobenzylamine in 10 mL of tetrahydrofuran is added dropwise. The reaction is allowed to warm slowly to room temperature and stirred for 18 h. The reaction mixture is concentrated in vacuo. The residue is taken up in 100 mL of dichloromethane and filtered. The filtrate is chromatographed twice, eluting with 5% methanol/dichloromethane. Fractions homogeneous by TLC are combined and concentrated in vacuo to yield a pale yellow solid. The solid is recrystallized from ethyl acetate to yield 0.298 g of the title compound as a white crystalline solid.

Workup

  1. temperatureto warm slowly to room temperature
  2. stirringstirred for 18 h
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. filtrationfiltered
  5. customThe filtrate is chromatographed twice
  6. washeluting with 5% methanol/dichloromethane
  7. concentrationconcentrated in vacuo
  8. customto yield a pale yellow solid
  9. customThe solid is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d674387aebbf4a92a034ff2f96402e9d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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