3-oxopentanenitrile → HCID 67253489, compound

HRID 2042099Notes

Reaction equation

[C:1]1([C:7]([C:20]2[CH:25]=CC=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.O=C(CC)CC#[N:30]>>[CH2:1]([C:7]1[CH:20]=[C:25]([NH2:30])[N: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)[N:8]=1)[CH3:6]

Participants

Reactant 2

HCID 99203693-oxopentanenitrile

HCID 59458312HCID 59458312, compound

Product 1

HCID 67253489HCID 67253489, compoundYield 85.3%

Procedure

Using a procedure analogous to Example B3, 6-(2-(diphenylmethylene)hydrazinyl)quinoline (4.0 g, 12.3 mmol) and 3-oxo-pentanenitrile (1.3 g, 1.1 eq) were combined to yield 5-ethyl-2-quinolin-6-yl-2H-pyrazol-3-ylamine (2.5 g, 85% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.87 (dd, J=7.8, 1.8 Hz, 1H), 8.39 (dd, J=8.4, 1.5 Hz, 1H), 8.12 (s, 1H), 8.06-8.03 (m, 2H), 7.54 (dd, J=8.4, 1.2 Hz, 1H), 5.46 (br s, 2H), 5.40 (s, 1H), 2.49 (q, J=7.5 Hz, 2H), 1.16 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 239.2 (M+H+).

Sources & evidence

ORD record: ord-42ad6ef65ac34353a6c40dbad28f642b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586565B2

Reaction notes

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