9-Methyl-9-azabicyclo[3.3.1]nonan-3-amine;dihydrochloride → N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(4-chlorophenyl)benzoxazole-7-carboxamide

HRID 506264Notes

Reaction equation

HRID 506264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.Cl.Cl.[NH2:22][CH:23]1[CH2:30][CH:29]2[N:31]([CH3:32])[CH:25]([CH2:26][CH2:27][CH2:28]2)[CH2:24]1>>[CH3:32][N:31]1[CH:25]2[CH2:26][CH2:27][CH2:28][CH:29]1[CH2:30][CH:23]([NH:22][C:17]([C:16]1[C:10]3[O:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[N:12][C:11]=3[CH:13]=[CH:14][CH:15]=1)=[O:19])[CH2:24]2

Participants

3

Reactant 2

HCID 189569979-Methyl-9-azabicyclo[3.3.1]nonan-3-amine;dihydrochlorideHCID 596257682-(4-Chlorophenyl)benzoxazole-7-carboxylic acid

Product 1

HCID 11502430N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(4-chlorophenyl)benzoxazole-7-carboxamideYield 43%

Procedure

N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(4-chlorophenyl)benzoxazole-7-carboxamide was prepared from 2-(4-chlorophenyl)benzoxazole-7-carboxylic acid and 3-amino-9-methyl-9-azabicyclo[3.3.1]nonane dihydrochloride using the method outlined in Step C of Example 14. This compound was obtained in 43% yield as an off-white solid: mp 193-196° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.14 (d, J=8.4 Hz, 2H), 8.06 (d, J=7.7 Hz, 1H), 7.88 (d, J=7.7 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.46 (t, J=7.8 Hz, 1H); 6.88 (d, J=6.6 Hz, 1H), 4.62 (m, 1H), 3.19 (d, J=10.0 Hz, 2H), 2.84-2.60 (m, 2H), 2.56 (s, 3H), 2.08 (m, 3H), 1.60 (m, 1H), 1.50 (t, J=11.4 Hz, 2H), 1.30-1.15 (m, 2H); MS (ESI) m/z 410 [M+H]+.

Workup

  1. customThis compound was obtained in 43% yield as an off-white solid

Sources & evidence

ORD record
ord-b0aa2b83368b46b394a0fd169ef724e0
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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