Tetrabutylammonium Fluoride → Tert-butyl 4-(1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate

HRID 519100노트

반응식

HRID 519100 반응식
[CH3:1][CH:2]1[C:7](=[O:8])[N:6](COCC[Si](C)(C)C)[N:5]=[C:4]2[CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[C:22]([CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[CH:21][C:20]=3[N:3]12.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][N:5]=[C:4]2[CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]([F:26])([F:28])[F:27])[C:22]([CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH2:31][CH2:30]4)=[CH:21][C:20]=3[N:3]12

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86727471Tert-butyl 4-(1-methyl-2-oxo-8-(trifluoromethyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate

생성물 1

HCID 86727472Tert-butyl 4-(1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of tert-butyl 4-(1-methyl-2-oxo-8-(trifluoromethyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate (0.07 g, 0.117 mmol) in THF (2 mL) was added a solution of TBAF in THF (1M, 0.58 mL, 0.585 mmol) and the reaction mixture was heated at reflux for 24 h. The reaction mixture was cooled to rt and the solvent was removed in vacuo. The residue was purified by preparative HPLC (Table 3, Method 23) to give tert-butyl 4-(1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate (0.04 g, 73%). LC/MS (Table 1, Method 3) Rt=1.665 min; MS m/z: 469 [M+H]+.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by preparative HPLC (Table 3, Method 23)

출처 및 근거

ORD 기록
ord-f49f0cf1bbf740e5a336d4560b09662d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115151B2

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