Triethylamine → 1,1-Dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate

HRID 516735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516735
[NH2:1][CH2:2][C:3]1[C:4](=[O:14])[NH:5][C:6]([CH:10]2[CH2:13][CH2:12][CH2:11]2)=[CH:7][C:8]=1[CH3:9].[NH2:15][CH2:16][C:17]1[C:18](=[O:28])[NH:19][C:20]([CH3:27])=[CH:21][C:22]=1[CH:23]1[CH2:26][CH2:25][CH2:24]1.[CH3:29][C:30]([O:33][C:34](O[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:35])([CH3:32])[CH3:31].C(N(CC)CC)C>C1COCC1.CN(C=O)C>[CH:10]1([C:6]2[NH:5][C:4](=[O:14])[C:3]([CH2:2][NH:1][C:34](=[O:35])[O:33][C:30]([CH3:32])([CH3:31])[CH3:29])=[C:8]([CH3:9])[CH:7]=2)[CH2:11][CH2:12][CH2:13]1.[CH:23]1([C:22]2[CH:21]=[C:20]([CH3:27])[NH:19][C:18](=[O:28])[C:17]=2[CH2:16][NH:15][C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])[CH2:24][CH2:25][CH2:26]1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 67464880HCID 67464880, VerbindungHCID 674669403-(aminomethyl)-4-cyclobutyl-6-methyl-2(1H)-pyridinone

Produkt 2

HCID 679517401,1-Dimethylethyl [(4-cyclobutyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamateAusbeute 9,5 %HCID 679517421,1-Dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamateAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To an ice bath cooled solution of 3-(aminomethyl)-6-cyclobutyl-4-methyl-2(1H)-pyridinone and 3-(aminomethyl)-4-cyclobutyl-6-methyl-2(1H)-pyridinone (3.5 g, 18 mmol) in THF (10 mL) and DMF (10 mL) were added Boc2O (4.68 g, 21.8 mmol) and triethylamine (5.4 g, 54 mmol). The contents were then stirred for 30 min at 30° C. The reaction was quenched by addition of ice water, during which time precipitation occurred. The reaction mixture was filtered and dried to give a mixture of the crude products. The crude products were separated by HPLC to give 1,1-dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate (2.1 g, 20%) and 1,1-dimethylethyl [(4-cyclobutyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate (1 g, 9.5%). Data for 1,1-dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate: 1H NMR (400 MHz, DMSO-d6) δ 11.28 (br s, 1H), 6.49 (br s, 1H), 5.86 (br s, 1H), 3.85 (br s, 2H), 1.97-2.14 (m, 7H), 1.87-1.94 (m, 1H), 1.72-1.77 (m, 1H), 1.28 (s, 9H).

Aufarbeitung

  1. customThe reaction was quenched by addition of ice water, during which time precipitation
  2. filtrationThe reaction mixture was filtered
  3. customdried
  4. customto give
  5. customThe crude products were separated by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fe71d94318b74440b8faf30c6e51ef89
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09114141B2

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