Triethylamine → HCID 22291445, Verbindung

HRID 968110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968110
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[CH2:6][CH2:7][C:8]3[C:9]([C:20]([NH2:22])=[O:21])=[N:10][N:11]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:12]=3[C:4]=2[CH:3]=1.[CH3:25][C:26]1[C:31]([C:32](O)=[O:33])=[CH:30][N:29]=[C:28]([Cl:35])[CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[Cl:35][C:28]1[N:29]=[CH:30][C:31]([C:32]([NH:1][C:2]2[CH:24]=[CH:23][C:5]3[CH2:6][CH2:7][C:8]4[C:9]([C:20]([NH2:22])=[O:21])=[N:10][N:11]([C:13]5[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=5)[C:12]=4[C:4]=3[CH:3]=2)=[O:33])=[C:26]([CH3:25])[CH:27]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222917476-Chloro-4-methylpyridine-3-carboxylic acidHCID 22291910HCID 22291910, Verbindung

Produkt 1

HCID 22291445HCID 22291445, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound of example 244 (3.872 mmoles), 4-methyl-6-chloronicotinic acid from step 2 (5.828 mmoles), and HATU (5.844 mmoles) were dissolved in 20 mL DMF followed by the addition of 1.9 mL triethylamine. The mixture was stirred at room temperature overnight. The solvent was then stripped and the residue suspended in water, filtered, and washed with water. The solid was recrystallized from acetonitrile, then redissolved in acetonitrile, decolorized with decolorizing carbon, and dried over anhydrous MgSO4. The solvent was then stripped down to a solid. Mp: 280-284° C. 1H NMR (d6-DMSO, 400 MHz): δ 2.28 (s, 3H); 2.84-2.98 (m, 4H); 7.25-7.44 (m, 6H); 7.49 (s, 1H); 7.51-7.62 (m, 3H); 8.35 (s, 1H); 10.31 (s, 1H). 13C NMR (DMSO, 100 MHz): δ 19.13, 20.35, 29.67, 115.01, 117.07, 117.30, 120.08, 121.34, 126.19, 126.60, 128.72, 128.81, 129.58, 132.80, 133.42, 136.81, 136.84, 137.64, 139.71, 143.19, 148.42, 149.96, 151.59, 161.44, 163.88, 164.47, 164.78. M+1=476.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with water
  3. customThe solid was recrystallized from acetonitrile
  4. dissolutionredissolved in acetonitrile
  5. dry with materialdried over anhydrous MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-36615e124f2f488394ac728b54e15107
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956052B2

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