반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12]C2C=C(C=CN=2)C(O)=O)=[N:4][NH:3]1.[CH:22]1([C:28]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CN(C(O[N:44]1N=N[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CC[O:71]C(C)=O.CO>>[CH:22]1([C:28]([N:30]2[CH2:31][CH2:32][N:33]([C:12]([C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2](=[O:1])[N:3]([CH2:50][C:49]4[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=4)[N:4]=3)=[O:71])[CH2:34][CH2:35]2)=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1참가 물질
반응물 5
HCID 81531Diisopropylethylamine
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 34375021-(Cyclohexylcarbonyl)piperazine
HCID 21584119Ethylacetate methanol
HCID 597677412-(4-Oxo-3,4-dihydro-phthalazin-1-ylmethyl)-isonicotinic acid생성물 1
실험 절차
To a stirred solution of 2-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-isonicotinic acid (iva) (0.25 g, 0.89 mol) in diemthylacetamide (2 mL) was added cyclohexyl-piperazin-1-yl-methanone (0.20 g, 1.0 mmol) followed by HBTU (0.38 g, 1.0 mmol) and diisopropyl ethyl amine (0.35 mL, 20.0 mmol) and stirred. The reaction mixture was then concentrated in vacuo and resulting oil subjected to flash chromatography eluent 9:1 EtOAc/MeOH. (rf of 0.3) The titled compound was isolated as a white solid. Single peak in LC-MS analysis, (0.18 g, 56%); m/z (LC-MS, ESP), RT=4.07 mins, (M+H)=460; 1H NMR (300 MHz) 12.57 (1H, S-NH), 8.56 (1H, d, J 5.1 Hz), 8.26 (1H, dd, J 1.5, 8.1 Hz), 7.95-7.80 (3H, m), 7.38 (1H, S), 7.25 (1H, d, J 5.7 Hz), 4.51 (2H, S), 3.56-3.17 (8H, m), 2.58 (1H, m), 1.71-1.61 (5H, m), 1.38-1.22 (5H, m).
후처리
- concentrationThe reaction mixture was then concentrated in vacuo
- customresulting oil
출처 및 근거
- ORD 기록
- ord-4ff2aa88688a40b190589f80c97e9b7e
- 출처 데이터셋
- uspto-grants-2008_08
- 특허 번호
- US07407957B2
연결된 노트
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