Oxalyl chloride → 4-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid Methyl Ester Hydrochloride

HRID 1937403ノート

反応式

HRID 1937403 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:11]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].[C:22](Cl)(=O)C([Cl:25])=O>C(Cl)Cl.CN(C=O)C>[ClH:25].[CH3:22][O:20][C:19]([C:18]1[C:11]2[C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[CH:2])[CH:4]=3)=[N:15][CH:14]=[N:13][C:12]=2[NH:16][CH:17]=1)=[O:21]

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 224608344-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid

生成物 1

HCID 867580994-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid Methyl Ester Hydrochloride収率 35%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To 4-(3-ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (0.108 g, 0.39 mmol) in dry methylene chloride (2 ml) was added a solution of oxalyl chloride (0.17 ml, 1.9 mmol) in dry methylene chloride (4 ml) followed by 1 drop of dry DMF. The suspension was stirred at ambient temperature for 1 hour, then concentrated in vacuo. To the resulting solid was added dry acetone (2 ml) and dry methanol (1 ml). The solution was stirred at ambient temperature for 15 hours, then concentrated in vacuo. The residue was diluted with ethyl acetate and water, and the solid filtered and dried in vacuo to afford the title compound as a tan powder (40 mg, 35%). TS-MS: 293 (MH+); anal. RP18-HPLC RT: min.

後処理

  1. concentrationconcentrated in vacuo
  2. additionTo the resulting solid was added dry acetone (2 ml) and dry methanol (1 ml)
  3. stirringThe solution was stirred at ambient temperature for 15 hours
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate and water
  6. filtrationthe solid filtered
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-f310ae886dbb476d97de1426a77228fa
出典データセット
uspto-grants-2002_05
特許番号
US06395733B1

反応ノート

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