Methylamine → HCID 68630541, Verbindung

HRID 2037366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037366
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:16][N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[CH2:26][CH2:27][C:28](O)=[O:29])[CH3:2].C[CH2:32][N:33](C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN>CN(C=O)C.C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:16][N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[CH2:26][CH2:27][C:28]([NH:33][CH3:32])=[O:29])[CH3:2]

Komponenten

8

Edukt 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 68629896HCID 68629896, Verbindung

Produkt 1

HCID 68630541HCID 68630541, VerbindungAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid (40 mg 89 μmol) in DMF (5 mL), DIPEA (35 mg, 268 μmol) is added. The mixture is cooled to 0° C. before PyBOP (51 mg, 98 μmol) is added. The mixture is stirred at 0° C. for 15 min before methylamine (58 μL of a 2 M solution in THF) is added. The mixture is stirred at rt for 16 h, diluted with sat. aq. NaHCO3 solution, and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates using heptane:EA 1:4 to give the title compound (35 mg) as a white solid; LC-MS: tR=1.10 min, [M+H]+=421.25; 1H NMR (CDCl3): δ 1.00 (d, J=6.5 Hz, 6H), 1.31 (t, J=7.3 Hz, 3H), 1.89-2.00 (m, 1H), 2.34-2.41 (m, 2H), 2.44 (s, 3H), 2.47 (s, 3H), 2.63 (d, J=7.0 Hz, 2H), 2.76 (q, J=7.8 Hz, 2H), 2.85 (d, J=4.5 Hz, 3H), 3.06-3.13 (m, 2H), 5.38 (s br, 1H), 7.91 (s, 1H), 7.93 (s, 1H), 8.10 (s, 1H), 8.55 (s, 1H).

Aufarbeitung

  1. additionis added
  2. additionis added
  3. extractionextracted twice with EA
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified on prep

Quellen und Nachweise

ORD-Eintrag
ord-b3785d140a8045d492ad0ca1004229f1
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575200B2

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