Ammonia → HCID 67370525, 화합물

HRID 1753180노트

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HRID 1753180 반응식
[N:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]3[CH2:13][CH2:14][N:15]([C:16]([C:18]4[C:19]([CH3:23])=[N:20][O:21][CH:22]=4)=[O:17])[C:9]3([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH2:8][N:7]2[CH:32]=1)=[N+:2]=[N-:3].[C:33]([Si:35]([CH3:38])([CH3:37])[CH3:36])#[CH:34].C(N(C(C)C)C(C)C)C.[NH4+].[Cl-].N>CN(C=O)C.[Cu](I)I>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:9]23[N:15]([C:16]([C:18]4[C:19]([CH3:23])=[N:20][O:21][CH:22]=4)=[O:17])[CH2:14][CH2:13][N:10]2[C:11](=[O:12])[C:6]2[N:7]([CH:32]=[C:4]([N:1]4[CH:34]=[C:33]([Si:35]([CH3:38])([CH3:37])[CH3:36])[N:3]=[N:2]4)[CH:5]=2)[CH2:8]3)=[CH:25][CH:26]=1

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 86657086HCID 86657086, 화합물

생성물 1

HCID 67370525HCID 67370525, 화합물수율 23%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of 7-azido-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (50 mg, 0.116 mmol) in DMF (2.5 mL) at 0° C. was added ethynyl-trimethyl-silane (33 μL, 0.23 mmol) followed by ethyl-diisopropyl-amine (24 μL, 0.14 mmol) and copper iodide (11 mg) and the mixture was stirred at 0° C. After one hour the reaction was complete (monitored by LCMS). A saturated aqueous solution of NH4Cl containing a drop of ammonia was added and the mixture extracted with EtOAc (3 times). The organics were washed with brine, dried (Na2SO4), filtrated and concentrated in vacuo. The resulting material was purified by flash chromatography (Biotage SP4, gradient 50-100% EtOAc in hexanes 10 CV; hold 100% EtOAc 7CV) to give 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one (14 mg, yield: 23%). ESI-MI m/z [M+H]+ 532.2.

후처리

  1. extractionthe mixture extracted with EtOAc (3 times)
  2. washThe organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe resulting material was purified by flash chromatography (Biotage SP4, gradient 50-100% EtOAc in hexanes 10 CV; hold 100% EtOAc 7CV)

출처 및 근거

ORD 기록
ord-ddd59033480c465ab1028ce4387432d2
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163029B2

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