Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 2-Amino-N-(5-bromo-thiophen-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 2079976

Reaktionsgleichung

Reaktionsgleichung von HRID 2079976
[Br:1][C:2]1[S:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.[NH2:9][C:10]1[N:18]=[C:17]([CH2:19][O:20][CH3:21])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[NH2:9][C:10]1[N:18]=[C:17]([CH2:19][O:20][CH3:21])[CH:16]=[CH:15][C:11]=1[C:12]([NH:8][CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:13]

Komponenten

5

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 231304372-Amino-6-methoxymethylnicotinic acidHCID 23130577(5-Bromothiophen-2-yl)methanamine

Produkt 1

HCID 231307182-Amino-N-(5-bromo-thiophen-2-ylmethyl)-6-methoxymethyl-nicotinamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of C-(5-bromo-thiophen-2-yl)-methylamine (250 mg, 1.3 mmol) in N,N-dimethylformamide (5 mL) were added tiethylamine (0.54 mL, 3.9 mmol), 2-amino-6-methoxymethyl-nicotinic acid (240 mg, 1.3 mmol) described in Preparation Example A-11, and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (690 mg, 1.6 mmol) sequentially on an ice bath, then, the solution was stirred for 2 days at room temperature. The reaction solution was partitioned in water and ethyl acetate. The organic layer was separated, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1), and the title compound (370 mg, 1.0 mmol, 79%) was obtained as a white solid.

Aufarbeitung

  1. customThe reaction solution was partitioned in water
  2. customThe organic layer was separated
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6bffc70267e44f669ec5e34632e48f31
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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