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

HRID 1844359Notes

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

Participants

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

customreaction
customreaction
stirringstirred at 80° C. for 1.5 hours
customReaction
temperaturecooled to room temperature
washwashed with water, brine, water
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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