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Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 4-[(3,4-Dimethoxy-phenylamino)-methyl]-N-(3-thiophen-2-yl-phenyl)-benzamide

HRID 252808
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252808
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].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=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([NH:12][C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:7]=3)=[O:30])=[CH:32][CH:33]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]
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Komponenten

5

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27946813-(Thiophen-2-yl)anilineHCID 224788804-[(3,4-Dimethoxyphenylamino)-methyl]-benzoic Acid

Produkt 1

HCID 597367084-[(3,4-Dimethoxy-phenylamino)-methyl]-N-(3-thiophen-2-yl-phenyl)-benzamideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 31 (122 mg, 0.696 mmol), acid 4 (182 mg, 0.633 mmol) and BOP (308 mg, 0.696 mmol) in DMF (4 ml) was added B3N (265 μl, 1.90 mmol). The reaction was stirred 3 h at room temperature under nitrogen, quenched with H2O and evaporated. The residue was extracted with ethyl acetate, washed with saturated solutions of NH4Cl, NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuum to form a material which was purified by flash chromatography (eluent 40% EtOAc in hexane) to give the title compound 32 (70 mg, 25%) as a yellow solid. 1H NMR: (DMSO) δ (ppm): 10.25 (s, 1H), 8.09-8.08 (m, 1H), 7.73 (ddd, J=7.6, 3.7, 3.7 Hz, 1H), 7.54 (dd, J=5.1, 1.0 Hz, 1H), 7.49 (d, J=8.2 Hz, 2H), 7.45 (dd, J=3.7, 1.2 Hz, 1H), 7.42-7.32 (m, 2H), 7.13 (dd, J=5.1, 3.7 Hz, 1H), 6.64 (d, J=8.6 Hz, 1H), 6.31 (d, J=2.5 Hz, 1H), 6.00-5.97 (m, 2H), 4.31 (d, J=6.1 Hz, 2H), 3.65 (s, 3H), 3.59 (s, 3H). MS: (calc), 444.2; (obt.) 445.5 (MH)+.

Aufarbeitung

  1. customquenched with H2O
  2. customevaporated
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with saturated solutions of NH4Cl, NaHCO3 and brine
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuum
  7. customto form a material which
  8. customwas purified by flash chromatography (eluent 40% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-82ab630b17974cfcb0a795923e7e19f6
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868205B2

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