Triethylamine → Quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophen-2-ylmethyl)-amide

HRID 2080246

Reaktionsgleichung

Reaktionsgleichung von HRID 2080246
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[O:12][C:13]1[S:17][C:16]([CH2:18][NH2:19])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]1[C:32]2[C:27](=[CH:28][C:29]([C:33](O)=[O:34])=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[O:12][C:13]1[S:17][C:16]([CH2:18][NH:19][C:33]([C:29]2[CH:28]=[C:27]3[C:32](=[CH:31][CH:30]=2)[N:23]=[CH:24][CH:25]=[CH:26]3)=[O:34])=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 825716-Quinolinecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23130639C-(5-(3-Benzyloxy-phenoxy)-thiophen-2-yl)-methylamine

Produkt 1

HCID 67119634Quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophen-2-ylmethyl)-amideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of C-(5-(3-benzyloxy-phenoxy)-thiophen-2-yl)-methylamine described in Preparation Example 18 (180 mg, 0.578 mmol) and 6-quinolinecarboxylic acid (100 mg, 0.578 mmol) in tetrahydrofuran (5 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (307 mg, 0.694 mmol) and triethylamine (0.16 mL, 1.16 mmol), and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, which was then partitioned, the organic layer was washed with water, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane: ethyl acetate), and quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophen-2-ylmethyl)-amide (73 mg, 27%) was obtained as a pale yellow solid.

Aufarbeitung

  1. customwas then partitioned
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by NH silica gel column chromatography (hexane: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-df0832440d7443fca5b789f7de69170a
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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