Quinuclidine, 3-amino-, dihydrochloride → HCID 11544770, compound

HRID 506250Notes

Reaction equation

HRID 506250 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[NH2:21][CH:22]1[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1>>[N:24]12[CH2:29][CH2:28][CH:27]([CH2:26][CH2:25]1)[CH:22]([NH:21][C:16]([C:15]1[C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[CH:12]=[CH:13][CH:14]=1)=[O:18])[CH2:23]2

Participants

3

Reactant 2

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 118067277-Benzoxazolecarboxylic acid, 2-phenyl-

Product 1

HCID 11544770HCID 11544770, compoundYield 57%

Procedure

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenylbenzoxazole-7-carboxamide was prepared from 2-phenylbenzoxazole-7-carboxylic acid and 3-aminoquinuclidine dihydrochloride using the method outlined in Step C of Example 7. This compound was obtained in 57% yield as a white solid: mp 179-180° C.; 1H NMR (300 MHz, CDCl3) δ 8.21 (dd, J=7.5, 2.1 Hz, 2H), 8.10 (dd, J=7.8, 1.2 Hz, 1H), 7.92 (dd, J=7.8, 1.2 Hz, 1H), 7.61-7.54 (m, 3H), 7.51-7.46 (m, 2H), 4.38-4.33 (m, 1H), 3.63-3.54 (m, 1H), 3.13-3.05 (m, 2H), 2.23 (q, J=3.0 Hz, 1H), 2.00-1.90 (m, 1H), 1.84-1.73 (m, 2H), 1.71-1.64 (m, 1H); MS (ESI) m/z 348[M+H]+.

Workup

  1. customThis compound was obtained in 57% yield as a white solid

Sources & evidence

ORD record
ord-dc8a88d748604b35b7496c882f6df1c1
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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