3-Amino-2-methoxypyridine → trans-N-(2-methoxypyridin-3-yl)-2,2-dimethyl-3-phenylcyclopropanecarboxamide

HRID 2174609Notes

Reaction equation

HRID 2174609 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.[CH3:15][O:16][C:17]1[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=1>>[CH3:15][O:16][C:17]1[C:22]([NH:23][C:11]([C@H:3]2[C@H:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:2]2([CH3:1])[CH3:14])=[O:13])=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

3

Reactant 2

HCID 27374883-Amino-2-methoxypyridineHCID 68582304(1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid

Product 1

HCID 86709743trans-N-(2-methoxypyridin-3-yl)-2,2-dimethyl-3-phenylcyclopropanecarboxamideYield 88.4%

Procedure

2,2-Dimethyl-trans-3-phenylcyclopropanecarboxylic acid (400 mg, 2.1 mmol) and 2-methoxy-3-pyridinamine (261 mg, 2.1 mmol) were reacted as described under General Procedure D to furnish the title compound (550 mg, 88%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.69-8.64 (m, 1H), 7.90 (s, 1H), 7.85-7.83 (m, 1H), 7.32-7.19 (m, 5H), 6.92-6.88 (m, 1H), 4.06 (s, 3H), 2.84 (d, J=5.7 Hz, 1H), 1.90 (d, J=5.7 Hz, 1H), 1.41 (s, 3H), 0.98 (s, 3H). mp 152-154° C. ESIMS m/z [M+H]+ 297.2.

Sources & evidence

ORD record
ord-18c8e13427e24f209dd2c8ade627c47f
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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