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

HRID 853335Notes

Reaction equation

HRID 853335 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>[C:24]([O:23][C:21]([N:18]1[CH2:17][CH2:16][CH:15]([C:13]([NH:12][C:8]2[CH:7]=[C:6]([O:5][C:4]3[CH:28]=[CH:29][C:30]([NH:31][C:32]([NH:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:34])=[C:2]([Cl:1])[CH:3]=3)[CH:11]=[CH:10][N:9]=2)=[O:14])[CH2:20][CH2:19]1)=[O:22])([CH3:25])([CH3:27])[CH3:26]

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 962WaterSolvent

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-c271f3594edc436ea3ba67838c3836ce
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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