Trifluoroacetic acid → {6-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 1775190노트

반응식

HRID 1775190 반응식
C(OC(=O)[N:7]([CH2:25][C:26]1[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[C:24]3[CH:23]=[N:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)=[O:15])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:33][O:32][C:29]1[N:28]=[CH:27][C:26]([CH2:25][NH:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([C:16]3[C:24]4[CH:23]=[N:22][CH:21]=[N:20][C:19]=4[NH:18][CH:17]=3)=[O:15])=[CH:12][CH:13]=2)=[CH:31][CH:30]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 57963060(6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]carbamic acid tert-butyl ester

생성물 1

HCID 57963230{6-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone수율 9.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To (6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (73, 66 mg, 0.14 mmol) in 5 mL of dichloromethane, trifluoroacetic acid (0.5 mL, 6.0 mmol) was added. The reaction was stirred at room temperature for 4 hours, then concentrated under vacuum, and combined with aqueous saturated sodium bicarbonate and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate adsorbed onto silica. This was purified by silica gel column chromatography eluting with methanol and dichloromethane. Appropriate fractions were combined, the solvents removed under vacuum, and the resulting solid washed with hexanes and ethyl acetate, with sonicating. The solid was collected by filtration to provide the desired compound as a white solid (P-0008, 4.8 mg). MS (ESI) [M+H+]+=360.9.

후처리

  1. concentrationconcentrated under vacuum
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThis was purified by silica gel column chromatography
  5. washeluting with methanol and dichloromethane
  6. customthe solvents removed under vacuum
  7. washthe resulting solid washed with hexanes and ethyl acetate
  8. customwith sonicating
  9. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-4b166e05ff874a11bd7ad1759ebc928b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260437B2

반응 노트

불러오는 중…