(2R)-2-(trifluoromethyl)oxirane → HCID 178521649, 화합물
반응식
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[N:16]=3)[C:12]([Cl:29])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[F:30][C:31]([F:36])([F:35])[C@@H:32]1[O:34][CH2:33]1>CC(O)C>[Cl:29][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][CH2:33][C@@H:32]([OH:34])[C:31]([F:36])([F:35])[F:30])[CH2:3][CH2:4]2)=[N:10][CH:11]=1참가 물질
반응 조건
- 온도
- 60 °C
실험 절차
To a solution of N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine (50 mg, 0.120 mmol) in 2-propanol (0.8 mL) was added (R)-(+)-3,3,3-trifluoro-1,2-epoxypropane (10.4 uL, 0.120 mmol). The mixture was stirred at 60° C. for 17 hr. The reaction mixture was concentrated. The resulting residue was purified by reverse phase HPLC and lyophilized to give 63 mg of (R)-3-(trans-4-(5′-chloro-6-((tetrahydro-2H-pyran-4-yl)methyl)amino-2,4′-bipyridin-2′-yl-amino)cyclohexylamino)-1,1,1-trifluoropropan-2-ol as its TFA salt. LCMS (m/z): 528.3 (MH+), retention time=0.53 min; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.34 (m, 4H) 1.36-1.56 (m, 2H) 1.61 (d, J=12.52 Hz, 2H) 1.70-1.90 (m, 1H) 2.04 (d, J=9.39 Hz, 3H) 2.13 (d, J=11.74 Hz, 1H) 2.97-3.19 (m, 4H) 3.24 (t, J=10.76 Hz, 3H) 3.64 (d, J=10.96 Hz, 1H) 3.83 (dd, J=10.96, 2.74 Hz, 2H) 4.36-4.50 (m, 2H) 6.54-6.68 (m, 2H) 6.70 (d, J=7.04 Hz, 0H) 6.94 (br. s., 0H) 7.23 (br. s., 0H) 7.53 (br. s., 0H) 8.04 (s, 0H) 8.76 (br. s., 2H)
후처리
- concentrationThe reaction mixture was concentrated
- customThe resulting residue was purified by reverse phase HPLC
출처 및 근거
- ORD 기록
- ord-63adb7c45efd45978690c5d68f0faaed
- 출처 데이터셋
- uspto-grants-2014_07
- 특허 번호
- US08778951B2
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