반응식
[CH2:1]([C:8]1[CH:9]=[C:10]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([N:30](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:24]=2)[C:11]([NH:14][C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>FC(F)(F)S(O)(=O)=O>[CH2:1]([C:8]1[CH:9]=[C:10]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH2:30])[N:24]=2)[C:11]([NH:14][C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1참가 물질
반응물 2
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 80 °C
실험 절차
A mixture of 4-(5-benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (110 mg, 0.172 mmol) in TFA (265 μL, 3.44 mmol) was treated with a couple of drops of trifluoromethanesulfonic acid (15.27 μL, 0.172 mmol) and the mixture was heated at 80° C. overnight. After cooling, the mixture was concentrated and the residue was dissolved in 5% MeOH/DCM and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 3% MeOH in DCM w/NH3) to give 4-(5-benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (15 mg, 0.038 mmol, 21.84% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.68 (s, 1H); 8.61 (d, J=2.15 Hz, 1H); 8.53 (d, J=2.54 Hz, 1H); 8.23 (d, J=2.15 Hz, 1H); 8.16 (dd, J=8.80, 2.74 Hz, 1H); 7.83 (br. s., 1H); 7.69 (br. s., 1H); 7.11-7.45 (m, 5H); 6.81 (d, J=8.80 Hz, 1H); 3.94 (s, 2H); 3.84 (s, 3H); 2.41 (s, 3H). m/z (ESI, +ve ion) 400.0 (M+H)+.
후처리
- temperatureAfter cooling
- concentrationthe mixture was concentrated
- dissolutionthe residue was dissolved in 5% MeOH/DCM
- customchromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 3% MeOH in DCM w/NH3)
출처 및 근거
- ORD 기록
- ord-a44efddbb84144b2a73d1d8033dbcd5d
- 출처 데이터셋
- uspto-grants-2014_07
- 특허 번호
- US08772480B2
연결된 노트
불러오는 중…