2-Phenylbenzoxazole-4-carboxylic acid → N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-phenylbenzoxazole-4-carboxamide

HRID 506223Notes

Reaction equation

HRID 506223 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:11][CH:10]2[N:12]([CH3:13])[CH:6]([CH2:7][CH2:8][CH2:9]2)[CH2:5]1.[C:14]1([C:20]2[O:21][C:22]3[C:23](=[C:25]([C:29](O)=[O:30])[CH:26]=[CH:27][CH:28]=3)[N:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:13][N:12]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH:4]([NH:3][C:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:22]3[O:21][C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:24][C:23]=13)=[O:30])[CH2:5]2

Participants

3

Reactant 2

HCID 108683692-Phenylbenzoxazole-4-carboxylic acidHCID 189569979-Methyl-9-azabicyclo[3.3.1]nonan-3-amine;dihydrochloride

Product 1

HCID 11703513N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-phenylbenzoxazole-4-carboxamideYield 40%

Procedure

N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-phenylbenzoxazole-4-carboxamide was prepared from 3-amino-9-methyl-9-azabicyclo[3.3.1]nonane dihydrochloride and 2-phenylbenzoxazole-4-carboxylic acid using conditions similar to those described for Step C in Example 1. This compound was obtained in 40% yield as a white solid; mp 182-185° C.; 1H NMR (300 MHz, CDCl3) δ 9.18 (d, J=6.5 Hz, 1H), 8.25 (m, 2H), 8.19 (dd, J=7.8, 0.9 Hz, 1H), 7.72 (dd, J=8.1, 1.0 Hz, 1H), 7.55-7.65 (m, 3H), 7.47 (t, J=8.0 Hz, 1H), 4.71-4.58 (m, 1H), 3.30 (m, 2H), 2.76 (m, 2H), 2.69 (s, 3H), 2.38-1.33 (m, 8H); MS (APCI) m/z 376 [M+H]+

Workup

  1. customThis compound was obtained in 40% yield as a white solid

Sources & evidence

ORD record
ord-c8501dbdbf644efbbceb809eeb8f9dab
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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