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 2358865

反応式

HRID 2358865 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-3a54ddb796144725a35cf7772c5af1a1
出典データセット
uspto-grants-2010_07
特許番号
US07763729B2

関連ノート

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