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Aniline → t-Butyl4-{[(4-{4-[(anilinocarbonyl)amino]-3-chlorophenoxy}-2-pyridyl)amino]carbonyl}-1-piperidinecarboxylate

HRID 387813
Notes
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Reaction equation

HRID 387813 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[NH:31][C:32]([O:34]C1C=CC=CC=1)=O)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[O:14])[CH:7]=1.[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CN(C)C=O>O>[NH:41]([C:32]([NH:31][C:30]1[CH:29]=[CH:28][C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]([CH:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])[CH2:19][CH2:20]3)=[O:14])[CH:7]=2)=[CH:3][C:2]=1[Cl:1])=[O:34])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6115AnilineHCID 6228DimethylformamideHCID 58930861t-Butyl 4-{[(4-(3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-2-pyridyl)amino]carbonyl}-1-piperidinecarboxylate

Product 1

HCID 58931346t-Butyl4-{[(4-{4-[(anilinocarbonyl)amino]-3-chlorophenoxy}-2-pyridyl)amino]carbonyl}-1-piperidinecarboxylateYield 48.1%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

t-Butyl 4-{[(4-{3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-2-pyridyl)amino]carbonyl}-1-piperidine carboxylate (250 mg), aniline (84 mg) and dimethylformamide (3 ml) were stirred at 130° C. for 70 minutes. The mixture was returned to room temperature, water was added and extraction was performed with ethyl acetate. Silica gel was added to the extract, the solvent was distilled off under reduced pressure, and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with silica gel, and column purification was performed (hexane:ethyl acetate=1:1, followed by ethyl acetate). The solvent was distilled off under reduced pressure to obtain 120 mg of a colorless oil.

Workup

  1. customwas returned to room temperature
  2. extractionextraction
  3. additionSilica gel was added to the extract
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with silica gel, and column purification
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1acfabfe7d8e4de4b551b8e3a969f7cd
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes