Diisopropylethylamine → 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 402406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402406
[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[N:14]=[N:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:4]=[N:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:55][CH:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C=O)C>[O:59]1[CH2:60][CH2:61][CH:56]([NH:55][C:15]([C:12]2[N:13]=[N:14][C:9]([O:8][CH2:7][C:6]3[N:2]([CH3:1])[N:3]=[N:4][C:5]=3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:10][CH:11]=2)=[O:17])[CH2:57][CH2:58]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 674986856-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

Produkt 1

HCID 573350996-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (tetrahydro-pyran-4-yl)-amideAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (98 mg, 0.31 mmol) and TBTU (111 mg, 0.35 mmol) in DMF (2 mL) was added DIPEA (270 μL, 1.57 mmol). Then 4-aminotetrahydropyran (35 mg, 0.35 mmol) was added and the mixture was stirred at room temperature under Ar for 16 h. The mixture was then evaporated and purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) afforded the title compound (101 mg, 81%) as an off white solid. MS: m/e=396.2 [M+H]+.

Aufarbeitung

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 50 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e205bbf7af204f58bb011587aae5cb50
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742097B2

Notizen zur Reaktion

Wird geladen…