Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol 6-(furan-3-yl)pyrazine-2-carboxamide

HRID 446913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446913
[NH2:1][C@@H](C1[N:11]2[C:7]([S:8][C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)=[N:10]2)=NN=1)C.[NH2:20][C:21]1[C:22]([C:32]([OH:34])=O)=[N:23][C:24]([C:27]2[CH:31]=[CH:30][O:29][CH:28]=2)=[CH:25][N:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[NH2:23][CH:22]([C:21]1[N:10]2[C@H:9]([S:8][CH:7]=[N:11]2)[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[N:20]=1)[CH3:32].[O:29]1[CH:30]=[CH:31][C:27]([C:24]2[N:23]=[C:22]([C:32]([NH2:1])=[O:34])[CH:21]=[N:26][CH:25]=2)=[CH:28]1

Komponenten

6

Edukt 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59363289(R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amineHCID 593633043-Amino-6-(furan-3-yl)pyrazine-2-carboxylic acid

Produkt 1

HCID 68705325(R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol 6-(furan-3-yl)pyrazine-2-carboxamideAusbeute 118,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(Step 8-v) To a mixture of (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine (0.141 g, 0.483 mmol) in DMF (3 mL) was added 3-amino-6-(furan-3-yl)pyrazine-2-carboxylic acid (0.066 g, 0.322 mmol), HBTU (0.159 g, 0.42 mmol), and TEA (0.135 ml, 0.966 mmol). After two hours the mixture was diluted with water and the resulting solids were collected. The solids were washed sequentially with 20% ethanol/ethyl ether, methylene chloride, and methanol, then dried in vacuo to provide (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-(furan-3-yl)pyrazine-2-carboxamide (0.09 g): 1H NMR 300 MHz DMSO-d6 10.8 (s, 1H), 9.21 (s, 1H), 8.61 (s, 1H), 8.38 (s, 1H), 7.68 (s, 1H), 7.51 (s, 1H), 7.39 (d, 2H), 7.13 (m, 3H), 7.05 (d, 2H), 5.69 (m, 1H), 1.76 (d, 3H); ESMS MH+=482.

Aufarbeitung

  1. customthe resulting solids were collected
  2. washThe solids were washed sequentially with 20% ethanol/ethyl ether, methylene chloride, and methanol
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0c983d4e1608481a801ea5afc3134ffa
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481538B2

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