8-Methyl-8-azabicyclo[3.2.1]octan-3-amine → N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-2-phenylbenzoxazole-7-carboxamide

HRID 506251Notes

Reaction equation

HRID 506251 reaction equation
[NH2:1][CH:2]1[CH2:8][CH:7]2[N:9]([CH3:10])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[C:11]1([C:17]2[O:18][C:19]3[C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:10][N:9]1[CH:7]2[CH2:6][CH2:5][CH:4]1[CH2:3][CH:2]([NH:1][C:26]([C:25]1[C:19]3[O:18][C:17]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:21][C:20]=3[CH:22]=[CH:23][CH:24]=1)=[O:27])[CH2:8]2

Participants

3

Reactant 2

HCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 118067277-Benzoxazolecarboxylic acid, 2-phenyl-

Product 1

HCID 11667667N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-2-phenylbenzoxazole-7-carboxamideYield 57%

Procedure

N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-2-phenylbenzoxazole-7-carboxamide was prepared from 3-amino-8-methyl-8-azabicyclo[3.2.1]octane and 2-phenylbenzoxazole-7-carboxylic acid using conditions similar to those described for Step C in Example 7. This compound was obtained in 57% yield as a white solid: mp 164-166° C.; 1H NMR (300 MHz, CH3OD) δ 8.25 (dd, J=8.1, 1.8 Hz, 2H), 7.90 (dd, J=8.1, 1.2 Hz, 1H), 7.80 (d, J=7.5 Hz, 1H), 7.64-7.58 (m, 3H), 7.50 (t, J=7.8 Hz, 1H), 4.25 (t, J=5.0 Hz, 1H), 3.63 (br s, 2H), 2.63 (s, 3H), 2.53-2.35 (m, 6H), 2.22-2.17 (m, 2H); MS (ESI) m/z 362 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ddee166641a04f50ab70649ce91e5c4c
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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