Trifluoroacetic acid → 4-[5-({[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]amino}carbonyl)-1H-indazol-3-yl]pyridinium trifluoroacetate
반응식
[C:1]([C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:19]=[C:18]3[C:43]2[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=2)=[O:14])[CH2:7]1)#[N:2].[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]>>[F:56][C:55]([F:58])([F:57])[C:53]([O-:59])=[O:54].[C:1]([C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:43]2[CH:44]=[CH:45][NH+:46]=[CH:47][CH:48]=2)=[O:14])[CH2:7]1)#[N:2]참가 물질
실험 절차
To a microwave vial equipped with a stir bar was added N-[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]-3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxamide (41.7 mg, 0.061 mmol) and TFA (1000 μl, 12.98 mmol). The reaction was stirred at room temperature for 20 minutes. After 20 minutes the LCMS indicates formation of the desired product. Triethylsilane (19.62 μl, 0.123 mmol) was addes, and the crude reaction was concentrated in vacuo. The crude was dissolved in 1 ml DMSO, filtered, and purified by reverse phase chromatography. The material was concentrated, and was then dissolved in acetonitrile and water. The compound was dried on the lyophilizer over 2 days to provide fluffy white solid. LCMS calc'd for C26H25N6O [M+H]+=437; found 437 1H NMR (600 MHz, CD3OD) δ 8.9 (d, 2H), 8.9 (s, 1H), 8.7 (d, 2H), 8.0 (d, 1H), 7.9 (d, 1H), 7.8 (s, 2H), 7.8 (d, 1H), 7.7 (m, 1H), 4.6 (s, 2H), 4.4 (m, 1H), 3.7 (m, 1H), 3.6 (m, 1H), 3.2 (m, 2H), 2.2 (m, 2H), 2.0 (m, 1H), 1.8 (m, 1H).
후처리
- customTo a microwave vial equipped with a stir bar
- waitAfter 20 minutes the LCMS indicates
출처 및 근거
- ORD 기록
- ord-759af97709a3425e8a0584b4cf8751d1
- 출처 데이터셋
- uspto-grants-2015_04
- 특허 번호
- US08999957B2
반응 노트
불러오는 중…