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Methylhydrazine → HCID 71244788, 화합물

HRID 80840
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HRID 80840 반응식
[CH:1]1([C:4](=O)[CH2:5][C:6]([N:8]2[CH2:48][CH2:47][C:11]3[N:12]=[C:13]([C:26]4[C:34]([CH3:35])=[CH:33][CH:32]=[C:31]5[C:27]=4[C:28]([CH3:46])=[N:29][N:30]5[S:36]([C:39]4[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=4)(=[O:38])=[O:37])[N:14]=[C:15]([N:16]4[CH2:21]C[C@@H](OC)[C:18](C)(C)[CH2:17]4)[C:10]=3[CH2:9]2)=O)[CH2:3][CH2:2]1.[CH2:50]1[CH2:54][O:53][CH2:52][CH2:51]1.[CH3:55][NH:56][NH2:57].[CH3:58]OC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>N1C=CC=CC=1>[CH:1]1([C:4]2[CH:5]=[C:6]([N:8]3[CH2:48][CH2:47][C:11]4[N:12]=[C:13]([C:26]5[C:34]([CH3:35])=[CH:33][CH:32]=[C:31]6[C:27]=5[C:28]([CH3:46])=[N:29][N:30]6[S:36]([C:39]5[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=5)(=[O:38])=[O:37])[N:14]=[C:15]([N:16]5[CH2:17][CH2:18][C@@H:54]([O:53][CH3:52])[C:50]([CH3:51])([CH3:58])[CH2:21]5)[C:10]=4[CH2:9]3)[N:56]([CH3:55])[N:57]=2)[CH2:2][CH2:3]1
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참가 물질

6

반응물 4

HCID 6061MethylhydrazineHCID 8028TetrahydrofuranHCID 87949Lawesson's reagentHCID 86690285(R)-1-cyclopropyl-3-(2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)propane-1,3-dione

생성물 1

HCID 71244788HCID 71244788, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
125 °C

실험 절차

A microwave vial was charged with (R)-1-cyclopropyl-3-(2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)propane-1,3-dione (0.563 g, 0.82 mmol) and THF (5 mL) and placed under a nitrogen atmosphere. Methyl hydrazine (87 μL, 1.64 mmol), pyridine (0.25 mL) and Lawesson's reagent (0.366 g, 0.90 mmol) were then added in sequence. The vessel was sealed and heated at 125° C. in a microwave reactor for 12 min. At that point the reaction mixture was concentrated and the residue was purified via FCC (0-10% MeOH/DCM; 10% NH4OH in DCM) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.56-8.61 (m, 1H), 8.05 (d, J=8.6 Hz, 1 H), 7.79 (d, J=8.3 Hz, 2 H), 7.56 (d, J=8.8 Hz, 1 H), 7.38 (d, J=8.6 Hz, 2 H), 5.52 (s, 1 H), 4.08 (d, J=13.4 Hz, 1 H), 3.96 (d, J=15.4 Hz, 1 H), 3.61-3.69 (m, 1 H), 3.55 (s, 3 H), 3.28-3.31 (m, 2 H), 3.26 (s, 3 H), 3.04 (t, J=10.2 Hz, 1 H), 2.94-2.99 (m, 1 H), 2.82-2.92 (m, 2 H), 2.33 (s, 3 H), 2.19 (s, 3 H), 1.86-1.94 (m, 1 H), 1.83 (s, 3 H), 1.67-1.78 (m, 1 H), 1.45-1.58 (m, 1 H), 0.91 (s, 3 H), 0.74-0.83 (m, 5H), 0.50-0.58 (m, 2 H); MS (ESI+) m/z 695.6 (M+H)+.

후처리

  1. customThe vessel was sealed
  2. concentrationAt that point the reaction mixture was concentrated
  3. customthe residue was purified via FCC (0-10% MeOH/DCM; 10% NH4OH in DCM)

출처 및 근거

ORD 기록
ord-0536606c9ad24562846f7d551e95a880
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846656B2

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