Quinuclidine, 3-amino-, dihydrochloride → HCID 11588920, compound

HRID 969848Notes

Reaction equation

HRID 969848 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=[CH:14][C:12]=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:17]1[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]=3[CH:14]=[CH:15][CH:16]=1)=[O:20])[CH2:25]2

Participants

3

Reactant 2

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 68454491HCID 68454491, compound

Product 1

HCID 11588920HCID 11588920, compoundYield 24%

Procedure

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(4-methoxyphenyl)benzoxazole-7-carboxamide was prepared from 2-(4-methoxyphenyl)benzoxazole-7-carboxylic acid and 3-aminoquinuclidine dihydrochloride using the method outlined in Step C of Example 14. This compound was obtained in 24% yield as a white solid: mp 166-167° C.; 1H NMR (500 MHz, CD3OD) δ 8.20 (dd, J=7.0, 2.0 Hz, 2H), 7.86 (d, J=7.9 Hz, 1H), 7.84 (d, J=7.9 Hz, 1H), 7.49 (t, J=7.9 Hz, 1H), 7.14 (dd, J=1.9, 7.0 Hz, 2H), 4.26 (m, 1H), 3.91 (s, 3H), 3.42 (m, 1H), 3.02 (m, 1H), 2.92 (m, 3H), 2.83 (m, 1H), 2.16 (d, J=3.1 Hz, 1H), 2.07 (m, 1H), 1.84 (m, 2H), 1.68 (m, 1H); MS (ESI) m/z 378 [M+H]+.

Workup

  1. customThis compound was obtained in 24% yield as a white solid

Sources & evidence

ORD record
ord-3529d3751c43452e8326b6cd44e253c8
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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