2-Amino-2-methyl-1-propanol → 3-Anilino-n-(2-hydroxy-1,1-dimethylethyl)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

HRID 30433

Reaktionsgleichung

Reaktionsgleichung von HRID 30433
[C:1]1([NH:7][C:8]2[C:16]3[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[S:10][C:9]=2[C:24](OCC)=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32]>>[NH:7]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:11]=2[S:10][C:9]=1[C:24]([NH:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32])=[O:25])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

3

Edukt 2

HCID 118072-Amino-2-methyl-1-propanolHCID 9865198Ethyl 3-(phenylamino)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

Produkt 1

HCID 684567053-Anilino-n-(2-hydroxy-1,1-dimethylethyl)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamideAusbeute 16 %

Versuchsvorschrift

A mixture of Example 1 and 2-amino-2-methyl-1-propanol (1.22 mL, 13 mmol) was heated at 150° C. for 16 h. The mixture was partitioned between DCM (60 mL) and 10% citric acid (75 mL). The aqueous phase was extracted with DCM (20 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (silica, 40% EtOAc in DCM) gave the title compound as a pale brown solid (45 mg, 16%). δH (CDCl3) 8.44 (1H, br s), 7.56-7.46 (3H, m), 7.34-7.31 (2H, m), 7.26-7.20 (3H, m), 7.03-6.96 (3H, m), 6.33 (1H, d, J 9.7 Hz), 5.65 (1H, br s), 4.21-4.18 (1H, br m), 3.49 (2H, d, J 5.5 Hz), 1.18 (6H, s). LCMS (ES+) 434 (M+H)+.

Aufarbeitung

  1. customThe mixture was partitioned between DCM (60 mL) and 10% citric acid (75 mL)
  2. extractionThe aqueous phase was extracted with DCM (20 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (silica, 40% EtOAc in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-7602cf148da24a8683ae94a7291722d7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423047B2

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