Dimethylformamide dimethyl acetal → HCID 58980884、化合物

HRID 1181339

反応式

HRID 1181339 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[CH3:18]OC(OC)N(C)C.[CH2:26]([O:28][CH:29]([O:41][CH2:42][CH3:43])[CH2:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[O:39][CH3:40])[CH3:27]>C(O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:16])[N:36]([C:35]4[CH:37]=[CH:38][C:32]([O:31][CH2:30][CH:29]([O:28][CH2:26][CH3:27])[O:41][CH2:42][CH3:43])=[C:33]([O:39][CH3:40])[CH:34]=4)[CH:18]=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylateHCID 114367644-(2,2-Diethoxyethoxy)-3-methoxyaniline

生成物 1

HCID 58980884HCID 58980884、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (2.0 g, 7.47 mmol, Maybridge, Inc) in ethanol (20 mL) was added dimethylformamide dimethyl acetal (2.5 mL, 2.5 eq, Aldrich). The reaction mixture was refluxed in a 90° C. oil bath for 3 h at which point the solvents were removed by rotary evaporation. Coevaporation with toluene removed the excess dimethylformamide dimethyl acetal. To the resulting residue was added ethanol (20 mL) and 4-(2,2-diethoxyethoxy)-3-methoxyaniline (2.3 g, 1.2 eq, Example H1). The reaction mixture was heated to 100° C. for 36 hours. The solvent was removed by rotary evaporation and the product purified by column chromatography followed by recrystallization from hot MeOH yielding the intermediate (0.82 g, 22%). 1H NMR (CDCl3) δ 1.22 (6H, t), 3.63-3.83 (4H, m), 3.90 (3H, s), 4.14 (2H, d, J=5.3 Hz), 4.92 (1H, t, J=5.2 Hz), 6.97 (2H), 7.06 (1H, d, J=8.5 Hz), 7.46 (2H, d, J=8.5 Hz), 7.58 (1H, s), 7.68 (2H, d, J=8.4 Hz), 8.24 (1H, br, s). LCMS m/z=501 (m+H+).

後処理

  1. customwere removed by rotary evaporation
  2. customCoevaporation with toluene removed the excess dimethylformamide dimethyl acetal
  3. temperatureThe reaction mixture was heated to 100° C. for 36 hours
  4. customThe solvent was removed by rotary evaporation
  5. customthe product purified by column chromatography
  6. customfollowed by recrystallization from hot MeOH yielding the intermediate (0.82 g, 22%)

出典と根拠

ORDレコード
ord-5973a2071c764f3f86cac406276b2574
出典データセット
uspto-grants-2007_10
特許番号
US07285557B2

関連ノート

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