1,1'-Carbonyldiimidazole → 5-(5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazol-3-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 245453노트

반응식

HRID 245453 반응식
[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:34]2[CH2:39][C@H:38]([CH3:40])[O:37][C@H:36]([CH3:41])[CH2:35]2)=[C:22]([F:33])[C:23]2[O:27][N:26]=[C:25]([C:28]([NH:30][NH2:31])=[O:29])[C:24]=2[CH:32]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1([C:47](N2C=CN=C2)=[O:48])C=CN=C1.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:34]2[CH2:35][C@H:36]([CH3:41])[O:37][C@H:38]([CH3:40])[CH2:39]2)=[C:22]([F:33])[C:23]2[O:27][N:26]=[C:25]([C:28]3[O:29][C:47](=[O:48])[NH:31][N:30]=3)[C:24]=2[CH:32]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 673572055-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carbohydrazide2회

생성물 1

HCID 673579695-(5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazol-3-yl)-1,3,4-oxadiazol-2(3H)-one수율 97%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

5-((tert-Butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carbohydrazide (Intermediate 207, 490 mg, 0.85 mmol) and di(1H-imidazol-1-yl)methanone (207 mg, 1.27 mmol) were dissolved in 8 ml of THF and was treated with DIEA (297 μl, 1.70 mmol) at room temperature for 16 hours. Reaction diluted with ethyl acetate and quenched with aq. Ammonium chloride solution. Organic layer was separated and washed with water, dried over sodium sulfate and concentrated to give 5-(5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazol-3-yl)-1,3,4-oxadiazol-2(3H)-one (495 mg, 97%)

후처리

  1. customReaction
  2. customquenched with aq. Ammonium chloride solution
  3. customOrganic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dc71b368d3aa4cfb8017edeab5aecc04
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658641B2

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