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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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(R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol → (R)-9-(3-hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)but-1-yn-1-yl)-3-methyl-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamide

HRID 575446
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HRID 575446 반응식
I[C:2]1[CH:3]=[CH:4][C:5]2[CH:18]3[CH2:19][CH:16]([CH2:17]3)[C:8]3[N:9]([CH3:15])[C:10]([C:12]([NH2:14])=[O:13])=[N:11][C:7]=3[C:6]=2[CH:20]=1.[CH3:21][C:22]1[O:26][N:25]=[C:24]([C@:27]([OH:31])([C:29]#[CH:30])[CH3:28])[N:23]=1>N1CCCCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:31][C@:27]([C:24]1[N:23]=[C:22]([CH3:21])[O:26][N:25]=1)([CH3:28])[C:29]#[C:30][C:2]1[CH:3]=[CH:4][C:5]2[CH:18]3[CH2:19][CH:16]([CH2:17]3)[C:8]3[N:9]([CH3:15])[C:10]([C:12]([NH2:14])=[O:13])=[N:11][C:7]=3[C:6]=2[CH:20]=1
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참가 물질

6

반응물 2

HCID 86669593(R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-olHCID 866935079-Iodo-3-methyl-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamide

생성물 1

HCID 86693508(R)-9-(3-hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)but-1-yn-1-yl)-3-methyl-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamide수율 77%

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 8082Piperidine용매

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온도
40 °C

실험 절차

To a solution 9-iodo-3-methyl-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxamide (100 mg, 0.26 mmol) in piperidine (2 mL) was introduced (2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol (160 mg, 1.05 mmol) and copper(I) iodide (2.5 mg, 0.01 mmol). The solution was de-oxygenated by nitrogen bubbling for five minutes, then tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.01 mmol) added and bubbling continued for a further two minutes. The pressure tube was closed under an atmosphere of nitrogen and the reaction mixture warmed to 40° C. for 2.5 hr. After evaporation of the reaction mixture in vacuo, the residue was suspended in ethyl acetate (25 mL) and washed with saturated aqueous sodium bicarbonate (6 mL), water (2×10 mL) and brine (5 mL). The organic extract was dried over sodium sulfate, filtered, and the filtrate adsorbed onto silica gel in vacuo. Purification of the dry-loaded material by silica gel flash column chromatography (eluent: heptane/ethyl acetate gradient) was followed by suspension of the product in acetonitrile (0.8 mL). The solid was collected by filtration to furnish the title compound (80 mg, 0.20 mmol, 77%) as a colorless solid: 1H NMR (500 MHz, CDCl3) δ 1.61-1.73 (m, 2H), 2.05 (s, 3H), 2.65 (s, 3H), 2.94 (q, J=8.62 Hz, 2H), 3.47 (td, J=7.25, 3.47 Hz, 1H), 3.57-3.70 (m, 2H), 4.01 (s, 3H), 5.57 (br. s., 1H), 7.02 (d, J=7.88 Hz, 1H), 7.17 (d, J=7.88 Hz, 1H), 7.70 (br. s., 1H), 8.51 (s, 1H); M+H=404.

후처리

  1. custombubbling
  2. waitcontinued for a further two minutes
  3. customThe pressure tube was closed under an atmosphere of nitrogen
  4. customAfter evaporation of the reaction mixture in vacuo
  5. washwashed with saturated aqueous sodium bicarbonate (6 mL), water (2×10 mL) and brine (5 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. filtrationfiltered
  9. customPurification of the dry-loaded material by silica gel flash column chromatography (eluent: heptane/ethyl acetate gradient)
  10. additionwas followed by suspension of the product in acetonitrile (0.8 mL)
  11. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-26b5a762e27c4046b8e6f3e27addfd36
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09034866B2

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