Sodium Carbonate → ethyl 4-(3-(N-methylacrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882139노트

반응식

HRID 882139 반응식
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[CH3:1][N:2]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1)[C:23](=[O:26])[CH:24]=[CH2:25]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 117703051ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

생성물 1

HCID 91928604ethyl 4-(3-(N-methylacrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (96 mg, 0.32 mmol) in THF (3.0 mL) at room temperature was added acryloyl chloride (40 μL, 0.49 mmol), and the solution was allowed to stir at room temperature for 30 minutes. Saturated aqueous sodium carbonate (5 mL) was added and the mixture was extracted with ethyl acetate (×3). The combined organic layers were washed with water (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier to give ethyl 4-(3-(N-methylacrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C19H19N4O3 [M+H]+: 351, found 351. 1H NMR (600 MHz, DMSO-D6) δ 13.03 (bs, 1H), 8.92 (s, 1H), 8.33 (s, 1H), 7.61 (d, J=7.63 Hz, 1H), 7.55 (t, J=8.21 Hz, 1H), 7.47 (s, 1H), 7.75 (d, J=7.63 Hz, 1H), 7.39 (d, J=8.8 Hz, 1H), 6.17 (s, 1H), 5.57 (t, J=7.04 Hz, 1H), 3.94 (q, J=7.04 Hz, 2H), 3.27 (s, 3H), 0.96 (t, J=7.04 Hz, 3H).

후처리

  1. extractionthe mixture was extracted with ethyl acetate (×3)
  2. washThe combined organic layers were washed with water (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-20b1285f5a4c491bbfb75a07d68d6e88
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993756B2

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