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Pyridine → 3-(4-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-5-isopropyl-1,2,4-oxadiazole

HRID 1844359
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HRID 1844359 반응식
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]#[N:18])[CH2:13][CH2:12]3)=[N:7][C:6]=12.C(=O)([O-])[O-].[Na+].[Na+].Cl.NO.[N:28]1C=CC=CC=1.[C:34]([O:39]C(=O)C(C)C)(=O)[CH:35]([CH3:37])[CH3:36]>CN(C=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[N:28]=[C:34]([CH:35]([CH3:37])[CH3:36])[O:39][N:18]=4)[CH2:13][CH2:12]3)=[N:7][C:6]=12
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 1049PyridineHCID 7346Isobutyric anhydrideHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 866974444-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carbonitrile

생성물 1

HCID 866974453-(4-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-5-isopropyl-1,2,4-oxadiazole

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carbonitrile (450 mg, 1.46 mmol) in 9 mL DMF and sodium carbonate (155 mg, 1.46 mmol) stirred room temperature 15 minutes, hydroxylamine HCl (203 mg, 2.9 mmol) added and reaction stirred 30 minutes at 80° C. Then 12 mL toluene added and pyridine (474 uL, 5.86 mmol) and isobutyricanhydride (973 uL, 5.86 mmol) added and reaction stirred at 80° C. for 1.5 hours. Reaction cooled to room temperature reduced in vacuo then taken up in ethyl acetate and washed with water, brine, water. Organic layer dried over magnesium sulfate and reduced in vacuo. For 250 mg crude product to use as is in further reactions. LRMS (ESI) m/z 392/394 [(M+H)]+, calc'd for C15H18BrN7O: 392.26.

후처리

  1. customreaction
  2. customreaction
  3. stirringstirred at 80° C. for 1.5 hours
  4. customReaction
  5. temperaturecooled to room temperature
  6. washwashed with water, brine, water
  7. dry with materialOrganic layer dried over magnesium sulfate

출처 및 근거

ORD 기록
ord-2505094d51f74d1abbb7b612ba799612
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946415B2

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