4-Methyl-3-oxopentanenitrile → HCID 67254757, compound

HRID 1711678Notes

Reaction equation

HRID 1711678 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=C[CH:2]=1.CC(C)C(=O)CC#[N:31]>>[CH:1]([C:7]1[CH:20]=[C:25]([NH2:31])[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)([CH3:2])[CH3:6]

Participants

3

Reactant 2

HCID 101299214-Methyl-3-oxopentanenitrileHCID 59458312HCID 59458312, compound

Product 1

HCID 67254757HCID 67254757, compoundYield 36%

Procedure

Using a procedure analogous to Example B3, 6-(2-(diphenylmethylene)hydrazinyl)quinoline (4.0 g, 12.3 mmol) and 4-methyl-3-oxo-pentanenitrile (1.5 g, 13.5 mmol) were combined to provide to 3-isopropyl-1-(quinolin-6-yl)-1H-pyrazol-5-amine. (1.1 g, 36% yield). 1H NMR (400 MHz, CDCl3) δ 8.93 (dd, J=4.4, 1.6 Hz, 1H), 8.21-8.18 (m, 2H), 8.05-8.02 (m, 2H), 7.44 (dd, J=8.4, 4.4 Hz, 1H), 5.56 (s, 1H), 3.85 (br s, 2H), 2.97 (m, 1H), 1.31 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 253.2 (M+H+).

Sources & evidence

ORD record
ord-5bc98ba05f3a4d97a73941c5afd41846
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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