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

HRID 593856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593856
[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-a26589d79b294e8f8d655877361e3072
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242962B2

Notizen zur Reaktion

Wird geladen…