Cyclopropylamine → Tert-butyl 4-(((6-cyano-4-(4-(((cyclopropylamino)carbonyl) amino)-3-fluorophenoxy)-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

HRID 1433708Notes

Reaction equation

HRID 1433708 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([O:38]C2C=CC=CC=2)=O)=[C:31]([F:45])[CH:30]=1)#[N:2].[CH:46]1([NH2:49])[CH2:48][CH2:47]1>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:49][CH:46]2[CH2:48][CH2:47]2)=[O:38])=[C:31]([F:45])[CH:30]=1)#[N:2]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 22936279tert-Butyl 4-(((6-cyano-4-(3-fluoro-4-((phenoxycarbonyl)amino)phenoxy)-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

Product 1

HCID 22936270Tert-butyl 4-(((6-cyano-4-(4-(((cyclopropylamino)carbonyl) amino)-3-fluorophenoxy)-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(((6-cyano-4-(3-fluoro-4-((phenoxycarbonyl)amino)phenoxy)-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate (490 mg), cyclopropylamine (0.72 ml) and tetrahydrofuran (5 ml) were stirred together at 60° C. for 35 minutes. Silica gel was added to the reaction solution and the solvent was distilled off under reduced pressure for adsorption. The reaction solution-adsorbed silica gel was purified by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=20:1) in a dry column packed with silica gel, to obtain 340 mg of a light yellow solid.

Workup

  1. additionSilica gel was added to the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure for adsorption
  3. customThe reaction solution-adsorbed silica gel
  4. customwas purified by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=20:1) in a dry column

Sources & evidence

ORD record
ord-d497b403535144a586353cc0c54b4627
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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