3-Cyclopentyl-3-oxopropanenitrile → HCID 67252786, compound

HRID 2042100Notes

Reaction equation

HRID 2042100 reaction equation
C1(C(C2C=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)C=CC=CC=1.[CH:26]1([C:31](=O)[CH2:32][C:33]#[N:34])[CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH:26]1([C:31]2[CH:32]=[C:33]([NH2:34])[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)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 135921183-Cyclopentyl-3-oxopropanenitrileHCID 59458312HCID 59458312, compound

Product 1

HCID 67252786HCID 67252786, compoundYield 53.3%

Procedure

Using a procedure analogous to Example B3, 6-(2-(diphenylmethylene)hydrazinyl)quinoline (5.0 g, 15.5 mmol) and 3-cyclopentyl-3-oxopropanenitrile (3.0 g, 1.1 eq) were combined to yield 3-cyclopentyl-1-(quinolin-6-yl)-1H-pyrazol-5-amine (2.3 g, 53% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.87 (m, 1H), 8.38 (dd, J=1.5, 8.4 Hz, 1H), 8.10 (s, 1H), 8.04-8.02 (m, 2H), 7.55 (dd, J=4.2, 8.1 Hz, 1H), 5.41 (br s, 2H), 5.38 (s, 1H), 2.90 (m, 1H), 1.85-1.96 (m, 2H), 1.53-1.70 (m, 6H); MS (ESI) m/z: 279.3 (M+H+).

Sources & evidence

ORD record
ord-830d628ba86e4bd3bc4f3639db3ce4fd
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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