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Methyl iodide → (R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

HRID 877747
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HRID 877747 반응식
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]([NH:15][NH2:16])=[O:14])[CH:12]=[C:6]2[C:5]=1[NH:17][C@@H:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C:19]1([CH3:32])[CH3:31])(=[O:3])[NH2:2].N1([C:38](N2C=CN=C2)=[S:39])C=CN=C1.[CH2:45](N(CC)CC)C.IC>O1CCCC1>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[O:14][C:45]([S:39][CH3:38])=[N:16][N:15]=3)[CH:12]=[C:6]2[C:5]=1[NH:17][C@@H:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C:19]1([CH3:32])[CH3:31])(=[O:3])[NH2:2]
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반응물 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 68291130(R)-tert-butyl 4-((3-carbamoyl-6-(hydrazinecarbonyl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

생성물 1

HCID 68350378(R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate
수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (R)-tert-butyl 4-((3-carbamoyl-6-(hydrazinecarbonyl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate (380 mg, 0.853 mmol) and di(1H-imidazol-1-yl)methanethione (175 mg, 0.981 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 10 min then heated to reflux for 100 min. After cooling to room temperature, triethylamine (0.357 mL, 2.56 mmol) and iodomethane (0.107 mL, 1.706 mmol) were added. The resulting mixture was stirred at room temperature for 5 h. The tetrahydrofuran solvent was evaporated in vacuo. The residue was triturated with water. The solid product was collected by filtration to give (R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate as white solid (0.404 g, 94% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 10.78 (d, J=8.4 Hz, 1H), 8.10 (d, J=1.8 Hz, 1H), 7.94 (s, 1H), 5.50 (br. s., 2H), 4.01 (dd, J=9.4, 5.8 Hz, 2H), 3.72 (br. s., 1H), 3.18 (br. s., 1H), 2.91 (br. s., 1H), 2.80 (s, 3H), 2.06 (d, J=14.3 Hz, 1H), 1.89-1.75 (m, 1H), 1.49 (s, 9H), 1.12 (s, 3H), 1.05 (s, 3H); MS (ES+) m/z: 502.3 (M+H); LC retention time: 4.241 min (analytical HPLC Method H).

후처리

  1. temperaturethen heated
  2. temperatureto reflux for 100 min
  3. customThe tetrahydrofuran solvent was evaporated in vacuo
  4. customThe residue was triturated with water
  5. filtrationThe solid product was collected by filtration

출처 및 근거

ORD 기록
ord-d0e01d80e9544b11ae645ae579867b4d
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987268B2

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