Isobutyl chloroformate → {4-[5-(4-Fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidin-2-yl}carbamic acid isobutyl ester

HRID 1094503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094503
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:29][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([NH2:36])[N:31]=4)=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:12][C:11]=1[C:37]([F:40])([F:39])[F:38]>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.O>[CH2:5]([O:4][C:2](=[O:3])[NH:36][C:32]1[N:31]=[C:30]([O:29][C:25]2[CH:26]=[CH:27][C:28]3[C:23](=[CH:22][CH:21]=[CH:20][C:19]=3[C:17](=[O:18])[NH:16][C:13]3[CH:14]=[CH:15][C:10]([F:9])=[C:11]([C:37]([F:40])([F:39])[F:38])[CH:12]=3)[CH:24]=2)[CH:35]=[CH:34][N:33]=1)[CH:6]([CH3:8])[CH3:7]

Komponenten

7

Edukt 2

HCID 62365Isobutyl chloroformateHCID 160715501-Naphthalenecarboxamide, 6-[(2-amino-4-pyrimidinyl)oxy]-N-[4-fluoro-3-(trifluoromethyl)phenyl]-

Produkt 1

HCID 23652795{4-[5-(4-Fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidin-2-yl}carbamic acid isobutyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

110 μl (0.84 mMol) isobutyl chloroformate are added portionwise to a solution of 300 mg (0.68 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (Step 10.3) in 4.5 ml CH2Cl2 and 7.5 ml pyridine. After 1 h, the solution is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2-CH2Cl2/EtOH 19:1) gives the title compound: MS: [M+1]+=543.

Aufarbeitung

  1. customthe aq. phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f2524e1b6d84e93a9a3fb39d57362f6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133886B2

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