4-Aminopyridine → 2,2-Dimethyl-trans-3-phenyl-N-(pyridin-4-yl)cyclopropanecarboxamide

HRID 2174607Notes

Reaction equation

HRID 2174607 reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[C:11]([OH:13])=O.[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1>>[CH3:14][C:2]1([CH3:1])[C@@H:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:3]1[C:11]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[O:13]

Participants

3

Reactant 2

HCID 17274-AminopyridineHCID 68582304(1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid

Product 1

HCID 867097412,2-Dimethyl-trans-3-phenyl-N-(pyridin-4-yl)cyclopropanecarboxamideYield 93.4%

Procedure

2,2-Dimethyl-trans-3-phenylcyclopropanecarboxylic acid (250 mg, 1.31 mmol) and 4-aminopyridine (123 mg, 1.31 mmol) were reacted as described under General Procedure D to furnish the title compound (326 mg, 93%) as a white foam. 1H NMR (300 MHz, CDCl3) δ 8.48-8.45 (m, 2H), 8.35 (br s, 1H), 7.63-7.60 (m, 2H), 7.31-7.16 (m, 5H), 2.87 (d, J=5.7 Hz, 1H), 1.96 (d, J=5.7 Hz, 1H), 1.40 (s, 3H), 0.97 (s, 3H). ESIMS m/z [M+H]+ 267.1.

Sources & evidence

ORD record
ord-0a21ea39a33e4f9499b90be639314696
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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