3-Cyclobutyl-3-oxopropanenitrile → HCID 67252465, compound

HRID 2042101Notes

Reaction equation

HRID 2042101 reaction equation
[C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=CC=2)=[N:8][NH:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:6]=CC=CC=1.C1(C(=O)CC#[N:33])CCC1>>[CH:20]1([C:7]2[CH:1]=[C:6]([NH2:33])[N:9]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][CH:14]=[CH:13]4)[N:8]=2)[CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 138611153-Cyclobutyl-3-oxopropanenitrileHCID 59458312HCID 59458312, compound

Product 1

HCID 67252465HCID 67252465, compoundYield 40%

Procedure

Using a procedure analogous to Example B3, 6-(2-(diphenylmethylene)hydrazinyl)quinoline (4.0 g, 12.3 mmol) and 3-cyclobutyl-3-oxo-propionitrile (1.7 g, 1.1 eq) were combined to provide 5-cyclobutyl-2-quinolin-6-yl-2H-pyrazol-3-ylamine (1.3 g, 40% yield). 1H NMR (300 MHz, CDCl3) δ 8.92 (dd, J=4.5, 1.2 Hz, 1H), 8.16-8.20 (m, 2H), 8.00-8.04 (m, 2H), 7.43 (dd, J=8.4, 1.2 Hz, 1H), 5.64 (s, 1H), 3.83 (br s, 2H), 3.53 (m, 1H), 2.40-2.20 (m, 4H), 2.08-1.92 (m, 2H); MS (ESI) m/z: 265.1 (M+H+).

Sources & evidence

ORD record
ord-672291a9e94b438e89bfc82dcd500600
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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