Potassium Carbonate → 3-({[2-(3-Fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 219679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219679
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][NH2:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[F:22][C:23]1[CH:24]=[C:25]([C:29]2[N:34]=[CH:33][C:32]([C:35](Cl)=[O:36])=[CH:31][N:30]=2)[CH:26]=[CH:27][CH:28]=1>C(OCC)(=O)C.O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][NH:21][C:35]([C:32]2[CH:33]=[N:34][C:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=3)=[N:30][CH:31]=2)=[O:36])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Produkt 1

HCID 691635173-({[2-(3-Fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of potassium carbonate (13.94 mmol) and 3-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (4.65 mmol) in ethyl acetate (30 mL) and water (20 mL) is added a solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (4.65 mmol) in ethyl acetate (20 mL). The mixture is stirred at room temperature overnight. The reaction mixture is extracted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated in vacuo to give 3-({[2-(3-fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a solid. MS 415 (M+H); 1H NMR (300 MHz, CDCl3): δ 1.47 (s, 9H), 1.55-2.22 (m, 5H), 2.90-4.90 (m, 6H), 7.15-7.25 (m, H), 7.41-7.53 (m, H), 7.56 (bs, NH), 8.18 (d, H), 8.29 (d, H), 9.21 (s, 2H).

Aufarbeitung

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ac93448d500f452fb611ba6bd1fd101d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202863B2

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