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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
Notes
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Reaction equation

HRID 1844359 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

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

Product 1

HCID 86697445
3-(4-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-5-isopropyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2505094d51f74d1abbb7b612ba799612
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946415B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes