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Triethylamine → 6-Amino-N-(5-(2-cyclopropylvinyl)thiophen-2-ylmethyl)nicotinamide

HRID 2080215
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2080215
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]1([CH:14]=[CH:15][C:16]2[S:20][C:19]([CH2:21][NH2:22])=[CH:18][CH:17]=2)[CH2:13][CH2:12]1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:22][CH2:21][C:19]2[S:20][C:16]([CH:15]=[CH:14][CH:11]3[CH2:13][CH2:12]3)=[CH:17][CH:18]=2)=[O:8])=[CH:4][N:3]=1
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 67119557C-(5-(2-Cyclopropylvinyl)thiophen-2-yl)methylamine

Produkt 1

HCID 671196356-Amino-N-(5-(2-cyclopropylvinyl)thiophen-2-ylmethyl)nicotinamideAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Aminonicotinic acid (35 mg, 0.251 mmol), C-(5-(2-cyclopropylvinyl)thiophen-2-yl)methylamine described in Preparation Example 151 (45 mg, 0.251 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (133 mg, 0.301 mmol) and triethylamine (0.042 mL, 0.301 mmol) were dissolved in N,N-dimethylformamide (3 mL), and the solution was stirred at room temperature for 3 hours. Water (10 mL) was added to the reaction solution, which was then extracted with ethyl acetate (30 mL). The organic layer was washed, dried over anhydrous magnesium sulfate, then, the solvent was evaporated in vacuo, the obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1), and the title compound (50 mg, 0.167 mmol, 66.6%) was obtained as a white solid.

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate (30 mL)
  2. washThe organic layer was washed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customthe obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-7e48cadb1bcd4b22951a1201446d9ef8
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932272B2

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