Diisopropylethylamine → 5-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide

HRID 624892

Reaktionsgleichung

Reaktionsgleichung von HRID 624892
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:18]([OH:20])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:3][CH2:2]1.C1(C2C=CC(C(O)=O)=NC=2OCC2CCCO2)CC1.C1(N(C2N=C(C)ON=2)C)CC1.[CH:51]1([CH2:54][C@H:55]([NH2:62])[C:56]2[N:60]=[C:59]([CH3:61])[O:58][N:57]=2)[CH2:53]C1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH:54]1([CH:55]([NH:62][C:18]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]3[CH2:2][CH2:3]3)=[C:9]([O:10][CH2:11][CH:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[N:8]=2)=[O:20])[C:56]2[N:60]=[C:59]([CH3:61])[O:58][N:57]=2)[CH2:51][CH2:53]1

Komponenten

7

Edukt 6

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 710872545-Cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acidHCID 710875605-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acidHCID 86674748(S)-2-Cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamineHCID 86674778Cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methylamine

Produkt 1

HCID 711056515-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide

Versuchsvorschrift

In analogy to the procedure described in Example 47 b), 5-cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid (which can e.g. be prepared in a similar manner than 5-cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid (Example 4 b)) was reacted with cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methylamine (which can e.g. be prepared in a similar manner than (S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (Example 32 e)) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=413.1 [MH+].

Quellen und Nachweise

ORD-Eintrag
ord-abe02f64ebdf484da8a4e98f636653d9
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303012B2

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