3-cyclopropyl-1H-pyrazol-5-amine → HCID 58169520, compound

HRID 1484838Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=2)[N:3]=1.[CH:20]1([C:23]2[NH:27][N:26]=[C:25]([NH2:28])[CH:24]=2)[CH2:22][CH2:21]1>C(O)C>[CH:20]1([C:23]2[NH:27][N:26]=[C:25]([NH:28][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]4[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=4)[N:3]=3)[CH:24]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-(4-(4-chloro-5-nitropyrimidin-2-yl)phenyl)acetonitrile (55 mg, 0.2 mmol, 1 equiv.) and 5-cyclopropyl-1H-pyrazol-3-amine (37 mg, 0.3 mmol, 1.5 equiv.) in ethanol (2 ml) was stirred at 85° C. for 15 h. Ethanol was remove under reduce pressure. The residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 100:1) to afford 2-(4-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-nitropyrimidin-2-yl)phenyl)acetonitrile (45 mg, 62%) as solid. The compound was determination by LC-MS (LC-MS (m/z)=362.1 [M+H]+).

Workup

customEthanol was remove
customThe residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 100:1)

Sources & evidence

ORD record: ord-1218de07656c422c85d144ba8c58892a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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