2-Methoxyethylamine → 4-(2-Formyl-1-isopropylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine

HRID 32348

反応式

HRID 32348 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]([CH:24]([CH3:26])[CH3:25])[C:22]([CH:27]=[O:28])=[N:21][CH:20]=2)[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].C(N(CC)C)C>S(Cl)(Cl)=O.CO>[CH:27]([C:22]1[N:23]([CH:24]([CH3:25])[CH3:26])[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)=[CH:20][N:21]=1)=[O:28]

参加物

7

反応物 4

HCID 80182-MethoxyethylamineHCID 12022DiethylmethylamineHCID 24638Chlorosulfonic acidHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine

生成物 1

HCID 866107904-(2-Formyl-1-isopropylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine収率 24.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
0 °C

実験手順

Chlorosulphonic acid (70 μl, 1.0 mmol) was added dropwise to solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 75 mg, 0.24 mmol) in thionyl chloride (2 ml) cooled at 0° C. and the mixture was 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 (100 μl, 0.5 mmol) and diethylmethylamine (0.5 ml, 7.5 mmol) in MeOH (1.5 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. The residue was purified by chromatography eluting with DCM/MeOH (98:2) to give the title compound (26 mg, 24%) as glassy solid. NMR: 1.53 (d, 6H) 2.86 (q, 2H) 3.17 (s, 3H) 3.28 (t, 2H) 5.65 (m, H) 7.3 (t, 1H) 7.50 (t, 1H) 7.71 (d, 2H) 7.83 (s, 1H) 7.89 (d, 2H) 8.68 (d, 1H) 9.81 (s, 1H) 10.11 (s, 1H).

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. customThe residue was purified by chromatography
  7. washeluting with DCM/MeOH (98:2)

出典と根拠

ORDレコード
ord-f37d61d802cf4017b2ed640deadac3b7
出典データセット
uspto-grants-2008_09
特許番号
US07427626B2

関連ノート

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