Triethylamine → HCID 22291566, Verbindung

HRID 457317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457317
[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.[Cl:25][C:26]1[C:31]([C:32](O)=[O:33])=[CH:30][C:29]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[N:28][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:25][C:26]1[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])=[CH:30][C:29]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[N:28][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 22291707HCID 22291707, VerbindungHCID 22291910HCID 22291910, Verbindung

Produkt 1

HCID 22291566HCID 22291566, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The title compound of Example 244 (0.757 mmoles), 5-chloro-2-morpholin-4-ylisonicotinic acid, (1.38 mmoles), and HATU (1.57 mmoles) were dissolved in 5 mL DMF followed by the addition of 0.4 mL of triethylamine. The mixture was stirred at room temperature for 3 hrs and partially stripped of DMF. The reaction mixture was then added to water, filtered, and washed with water. The solid was dissolved in THF, decolorized with decolorizing carbon, and dried over anhydrous MgSO4. The THF was stripped and the solid triturated in diethyl ether three times, then triturated in ethanol, and twice more with acetonitrile, filtered and dried under vacuum. Mp: 309–313° C. 1H NMR (d6-DMSO, 400 MHz): δ 2.80–2.95 (m, 4H); 3.42 (t, 4H, J=5 Hz); 3.62 (t, 4H, J=5 Hz); 6.88 (s, 1H); 7.17–7.21 (m, 1H); 7.23–7.41 (m, 5H); 7.49–7.58 (m, 3H); 8.14 (s, 1H); 10.31 (s, 1H). 13C NMR (d6-DMSO, 100 MHz): δ 20.34, 29.70, 45.74, 66.50, 106.55, 114.97, 115.87, 117.09, 117.32, 120.05, 121.41, 126.67, 128.64, 128.73, 129.62, 133.47, 136.80, 136.82, 137.48, 139.64, 143.21, 145.28, 147.54, 158.30, 161.39, 163.85, 164.45. M+1=547.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with water
  3. dissolutionThe solid was dissolved in THF
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solid triturated in diethyl ether three times
  6. customtriturated in ethanol
  7. filtrationtwice more with acetonitrile, filtered
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-039178bde9cd4e15adcb9fedfa7ec1a6
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186743B2

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