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

HRID 1937403노트

반응식

HRID 1937403 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f310ae886dbb476d97de1426a77228fa
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395733B1

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