Quinuclidine, 3-amino-, dihydrochloride → N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(4-methoxyphenyl)benzoxazole-4-carboxamide

HRID 969828Notes

Reaction equation

HRID 969828 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:12](=[C:14]([C:18]([OH:20])=O)[CH:15]=[CH:16][CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1.Cl.Cl.[NH2:23][CH:24]1[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1>>[N:26]12[CH2:31][CH2:30][CH:29]([CH2:28][CH2:27]1)[CH:24]([NH:23][C:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:11]3[O:10][C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[N:13][C:12]=13)=[O:20])[CH2:25]2

Participants

3

Reactant 2

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 158135912-(4-Methoxyphenyl)benzoxazole-4-carboxylic acid

Product 1

HCID 11682316N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(4-methoxyphenyl)benzoxazole-4-carboxamideYield 5%

Procedure

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(4-methoxyphenyl)benzoxazole-4-carboxamide was prepared from 2-(4-methoxyphenyl)benzoxazole-4-carboxylic acid and 3-aminoquinuclidine dihydrochloride using the method outlined in Step C of Example 14. This compound was obtained in 5% yield as an off-white solid: mp 108-109° C.; 1H NMR (500 MHz, CD3OD) δ 8.19 (dt, J=9.7, 2.8 Hz, 2H), 8.01 (dd, J=7.7, 0.9 Hz, 1H), 7.82 (dd, J=7.7, 0.9 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 7.14 (dt, J=9.7, 2.8 Hz, 2H), 4.25 (m, 1H), 3.91 (s, 3H), 3.47 (m, 1H), 3.02 (m, 2H), 2.91 (m, 2H), 2.77 (m, 1H), 2.12 (m, 2H), 1.80 (m, 3H); MS (ESI) m/z 378 [M+H]+

Workup

  1. customThis compound was obtained in 5% yield as an off-white solid

Sources & evidence

ORD record
ord-eec3ab35fd4a4ef7a4fc6a53386e7bdb
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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