3-Pyridinemethanamine → HCID 11614063, Verbindung

HRID 1723957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723957
[C:1]([C:5]1[CH:6]=[C:7]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:8]([O:29][CH3:30])=[C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:28])=[C:18]([N:20]3[CH:24]=[C:23]([C:25]([OH:27])=O)[CH:22]=[N:21]3)[CH:19]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[N:40]1[CH:41]=[CH:42][CH:43]=[C:38]([CH2:37][NH:36][C:25]([C:23]2[CH:22]=[N:21][N:20]([C:18]3[CH:19]=[C:14]([C:12](=[O:13])[NH:11][C:9]4[CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=[C:7]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:8]=4[O:29][CH3:30])[CH:15]=[CH:16][C:17]=3[CH3:28])[CH:24]=2)=[O:27])[CH:39]=1

Komponenten

7

Edukt 4

HCID 310183-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57559703HCID 57559703, Verbindung

Produkt 1

HCID 11614063HCID 11614063, VerbindungAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The above carboxylic acid (75 mg, 0.15 mmol), 3-(aminomethyl)pyridine (25 mg, 0.23 mmol) and HATU (85 mg, 0.23 mmol) were dissolved in DMF (1.5 mL). N,N-Diisopropylethylamine (78 μL, 0.45 mmol) was added and the reaction was stirred overnight. Water was added and the resulting solution was extracted with CH2Cl2 (4×30 mL). The combined organic extracts were washed with 5% LiCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by semi-prep HPLC. The product fractions were concentrated and sodium bicarbonate added. The resulting solid was collected by vacuum filtration, washed with water, and dried under vacuum at 55° C. to provide the title compound (48 mg, 54%) as white solid: mp 127-133° C.; ESI MS m/z 591 [C30H34N6O5S+H]+; HPLC>95%, tR=15.03 min.

Aufarbeitung

  1. extractionthe resulting solution was extracted with CH2Cl2 (4×30 mL)
  2. washThe combined organic extracts were washed with 5% LiCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by semi-prep HPLC
  7. concentrationThe product fractions were concentrated
  8. additionsodium bicarbonate added
  9. filtrationThe resulting solid was collected by vacuum filtration
  10. washwashed with water
  11. customdried under vacuum at 55° C.

Quellen und Nachweise

ORD-Eintrag
ord-a2df1518511b4ceca56f99b2d99d5546
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485657B2

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