2-(Quinuclidin-3-yl)acetic acid → 2-(1-aza-bicyclo[2.2.2]oct-3-yl)-N-[1-(3-isopropyl-phenyl)-cyclopropyl]-acetamide

HRID 2281280Notes

Reaction equation

HRID 2281280 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:10]2([NH2:13])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[CH:16]([CH2:22][C:23](O)=[O:24])[CH2:15]2>>[N:14]12[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21]1)[CH:16]([CH2:22][C:23]([NH:13][C:10]1([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=3)[CH2:12][CH2:11]1)=[O:24])[CH2:15]2

Participants

3

Reactant 2

HCID 103521012-(Quinuclidin-3-yl)acetic acidHCID 55268959Cyclopropanamine, 1-[3-(1-methylethyl)phenyl]-

Product 1

HCID 903861002-(1-aza-bicyclo[2.2.2]oct-3-yl)-N-[1-(3-isopropyl-phenyl)-cyclopropyl]-acetamideYield 14%

Procedure

Using general procedure I, 1-(3-isopropyl-phenyl)-cyclopropylamine (278 mg, 1.58 mmol) and (1-aza-bicyclo[2.2.2]oct-3-yl)-acetic acid (267 mg, 1.58 mmol) gave the title compound as a white solid (70 mg, 14%). 1H NMR (400 MHz, CD3OD) δ 7.16 (t, J=8.0 Hz, 1H), 7.07 (s, 1H), 6.97 (dd. J=19.2, 7.6 Hz, 2H), 3.16-3.23 (m, 1H), 2.79-2.97 (m, 5H), 2.51-2.58 (m, 1H), 2.23-2.41 (m, 3H), 1.83-1.92 (m, 1H), 1.68-1.81 (m, 3H), 1.54-1.62 (m, 1H), 1.15-1.25 (m, 10H) ppm. 13C NMR (400 MHz, CD3OD) δ 173.6, 148.5, 142.4, 127.8, 123.6, 123.1, 122.0, 73.0, 53.1, 46.6, 45.9, 39.3, 34.1, 32.3, 28.1, 26.4, 24.4, 19.7, 16.8 ppm. Purity: 96.9% HPLCMS (210 nm); retention time 2.55 min; (M+1) 327.

Sources & evidence

ORD record
ord-75b0fb87f2d2403aa2db765025dcc7f3
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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