7-Benzoxazolecarboxylic acid, 2-phenyl- → N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-phenylbenzoxazole-7-carboxamide

HRID 506248Notes

Reaction equation

HRID 506248 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[CH2:29][CH:28]2[N:30]([CH3:31])[CH:24]([CH2:25][CH2:26][CH2:27]2)[CH2:23]1>>[CH3:31][N:30]1[CH:24]2[CH2:25][CH2:26][CH2:27][CH:28]1[CH2:29][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 118067277-Benzoxazolecarboxylic acid, 2-phenyl-HCID 189569979-Methyl-9-azabicyclo[3.3.1]nonan-3-amine;dihydrochloride

Product 1

HCID 11595937N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-phenylbenzoxazole-7-carboxamideYield 43%

Procedure

N-(9-Methyl-9-azabicyclo[3.3.1]non-3-yl)-2-phenylbenzoxazole-7-carboxamide was prepared from 2-phenylbenzoxazole-7-carboxylic acid and 3-amino-9-methyl-9-azabicyclo[3.3.1]nonane dihydrochloride using the method outlined in Step C of Example 7. This compound was obtained in 43% yield and obtained as an off-white solid: mp 208-210° C.; 1H NMR (500 MHz, CDCl3) δ 8.95 (br s, 1H), 8.23 (d, J=6.9 Hz, 2H), 8.20 (d, J=2.0 Hz, 1H), 7.71 (d, J=2.0 Hz, 1H), 7.57-7.65 (m, 3H), 4.58 (q, J=7.1 Hz, 1H), 3.18 (br s, 2H), 2.58 (m, 5H), 2.02-2.25 (m, 3H), 1.55 (s, 3H), 1.23 (m, 3H); MS (APCI) m/z 411 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-2ea213f2d51f4a34bcaf0bde9c2f6350
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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