Quinuclidine, 3-amino-, dihydrochloride → HCID 11675007, compound

HRID 506246Notes

Reaction equation

HRID 506246 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=O)[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.Cl.Cl.[NH2:22][CH:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1>>[N:25]12[CH2:30][CH2:29][CH:28]([CH2:27][CH2:26]1)[CH:23]([NH:22][C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:10]3[O:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:12][C:11]=13)=[O:19])[CH2:24]2

Participants

3

Reactant 2

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 59626030HCID 59626030, compound

Product 1

HCID 11675007HCID 11675007, compoundYield 8%

Procedure

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(4-fluorophenyl)benzoxazole-4-carboxamide was prepared from 2-(4-fluorophenyl)benzoxazole-4-carboxylic acid and 3-aminoquinuclidine dihydrochloride using the method outlined in Step C of Example 14. This compound was obtained in 8% yield as a white solid: mp 208-209° C.; 1H NMR (500 MHz, CD3OD) δ 8.33 (m, 2H), 8.05 (m, 1H), 7.90 (dd, J=8.2, 0.9 Hz, 1H), 7.55 (m, 1H), 7.39 (m, 2H), 4.29 (m, 1H), 3.52 (m, 1H), 3.06 (m, 2H), 2.94 (m, 2H), 2.92 (m, 1H), 2.16 (m, 2H), 1.86 (m, 3H); MS (ESI) m/z 366 [M+H]+

Workup

  1. customThis compound was obtained in 8% yield as a white solid

Sources & evidence

ORD record
ord-de8b0263261a4d46a02f5a085f18937f
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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