Triethylamine → 6-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide

HRID 2079961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079961
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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.CO.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][CH2:23][C:21]2[S:22][C:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:19][CH:20]=2)=[O:8])=[CH:4][N:3]=1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 231306122-Thiophenemethanamine,5-(phenylmethyl)-

Produkt 1

HCID 231303536-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamideAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel4×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 6-aminonicotinic acid (340 mg, 2.4 mmol) and C-(5-benzyl-thiophen-2-yl)-methylamine described in Preparation Example 42 (450 mg, 2.2 mmol) in N,N-dimethylformamide (5 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 2.4 mmol) and triethylamine(0.62 mL, 4.4 mmol), and the solution was stirred at 60° C. for 1 hour. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed twice with water. Silica gel was added to the organic layer, the solvent was evaporated in vacuo adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate, then ethyl acetate:methanol=10:1), and 6-amino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamide (210 mg, 0.65 mmol, 29.5%) was obtained.

Aufarbeitung

  1. customwas then partitioned
  2. washthe organic layer was washed twice with water
  3. additionSilica gel was added to the organic layer
  4. customthe solvent was evaporated in vacuo adsorption, purification

Quellen und Nachweise

ORD-Eintrag
ord-07255c3963894ecca90e46bbafeb493a
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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