2-Methoxyethylamine → 4-(1,2-Diethyl-4-methylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine

HRID 268584ノート

反応式

HRID 268584 の反応式
Cl[S:2]([OH:5])(=O)=[O:3].[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH2:24][CH3:25])[C:22]([CH2:26][CH3:27])=[N:21][C:20]=2[CH3:28])[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>S(Cl)(Cl)=O.C(O)(C)C>[CH2:24]([N:23]1[C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([S:2](=[O:5])(=[O:3])[NH:33][CH2:32][CH2:31][O:30][CH3:29])=[CH:9][CH:8]=3)[N:18]=2)=[C:20]([CH3:28])[N:21]=[C:22]1[CH2:26][CH3:27])[CH3:25]

参加物

6

反応物 3

HCID 80182-MethoxyethylamineHCID 24638Chlorosulfonic acidHCID 111625992-Anilino-4-(1,2-diethylmethylimidazol-5-yl)pyrimidine

生成物 1

HCID 113397474-(1,2-Diethyl-4-methylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine収率 40%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
0 °C

実験手順

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to solution of 2-anilino-4-(1,2-diethylmethylimidazol-5-yl)pyrimidine (Method 13; 28 mg, 0.09 mmol) in thionyl chloride (2 ml) cooled at 0° C. and the mixture stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of 2-methoxyethylamine (300 μl, 3.45 mmol) in isopropanol (2 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Water (20 ml) was added and extracted EtOAc (2×20ml). The organic layers were combined, dried and evaporated in vacuo to give the title compound (16 mg, 40%) as a orange solid. NMR 2.35-2.45 (m, 9H), 2.7 (q, 2H), 2.89 (q, 2H), 3.40-3.28 (m, 2H), 3.60-3.58 (m, 3H), 4.35 (m, 2H), 7.0 (d, 1H), 7.49 (t, 1H), 7.70 (d, 2H), 7.9 (d, 2H), 8.55 (d, 1H); m/z 445.

後処理

  1. temperaturethen heated at 90° C. for 90 minutes
  2. customThe volatiles were removed by evaporation
  3. customthe residue was dried under high vacuum (<2 mmHg) for 1 hour
  4. stirringThe mixture was stirred for 30 minutes
  5. customthe volatiles were evaporated in vacuo
  6. additionWater (20 ml) was added
  7. extractionextracted EtOAc (2×20ml)
  8. customdried
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-22d3170bdb684fec8c1eede22c282210
出典データセット
uspto-grants-2008_11
特許番号
US07446105B2

反応ノート

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