Chloride → Ethyl 4-{5-[(2-methylacryloyl)amino]pyridin-3-yl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882122노트

반응식

HRID 882122 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[N:6][CH:7]=1.CCN([CH:28]([CH3:30])[CH3:29])C(C)C.[Cl-].[CH3:32][OH:33]>C(Cl)Cl>[CH3:29][C:28](=[CH2:30])[C:32]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[N:6][CH:7]=1)=[O:33]

참가 물질

6

반응물 4

HCID 312ChlorideHCID 887MethanolHCID 81531DiisopropylethylamineHCID 117703138HCID 117703138, 화합물

생성물 1

HCID 71599600Ethyl 4-{5-[(2-methylacryloyl)amino]pyridin-3-yl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To ethyl 4-(5-aminopyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (59 mg, 0.14 mmol) in DCM (1.0 mL) was added Hunig's base (0.060 mL, 0.34 mmol) at 0° C. Methacyloyl chloride (0.015 mL, 0.15 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. After being stirred for 17 hours at room temperature, MeOH was added to quench the reaction and the solution was concentrated in vacuo. The crude reaction was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The products were collected and lyophilized to afford a colorless solid. LRMS (ESI) calc'd for C18H18N5O3 [M+H]+: 352, found 352. 1H NMR (600 MHz, DMSO-D6) δ 13.17 (s, 1H), 10.22 (s, 1H), 9.04 (s, 1H), 9.02 (d, 1H, J=1.7 Hz), 8.55 (s, 1H), 8.50 (m, 1H), 8.45 (m, 1H), 5.93 (s, 1H), 5.65 (s, 1H), 3.99 (q, 2H, J=7.2 Hz), 2.01 (s, 3H), 1.00 (t, 3H, J=7.2 Hz).

후처리

  1. customto quench
  2. customthe reaction
  3. concentrationthe solution was concentrated in vacuo
  4. customThe crude reaction
  5. customwas purified by reverse phase HPLC
  6. customThe products were collected
  7. customto afford a colorless solid

출처 및 근거

ORD 기록
ord-94cdc354ac3c4845a592aeae83ec1f16
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993756B2

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