2-Phenylbenzoxazole-4-carboxylic acid → N-(1-Methylpiperidin-4-yl)-2-phenylbenzoxazole-4-carboxamide

HRID 969807Notes

Reaction equation

HRID 969807 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:10](=[C:12]([C:16]([OH:18])=O)[CH:13]=[CH:14][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[NH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1>>[CH3:28][N:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:16]([C:12]2[CH:13]=[CH:14][CH:15]=[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]=23)=[O:18])[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 108683692-Phenylbenzoxazole-4-carboxylic acidHCID 220025361-Methylpiperidin-4-amine dihydrochloride

Product 1

HCID 11631388N-(1-Methylpiperidin-4-yl)-2-phenylbenzoxazole-4-carboxamideYield 38%

Procedure

N-(1-Methylpiperidin-4-yl)-2-phenylbenzoxazole-4-carboxamide was prepared from 2-phenylbenzoxazole-4-carboxylic acid and 4-amino-1-methylpiperidine dihydrochloride using the conditions described for Step C in Example 1. This compound was obtained in 38% yield as a white solid; mp 126-128° C.; 1H NMR (300 MHz, CDCl3) δ 9.26 (d, J=7.5 Hz, 1H), 8.25 (m, 2H), 8.19 (d, J=7.7 Hz, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.63-7.53 (m, 3H), 7.46 (t, J=8.0 Hz, 1H), 4.20 (m, 1H), 2.86 (m, 2H), 2.37 (s, 3H), 2.33-2.13 (m, 4H), 1.85-1.73 (m, 2H); MS (APCI) m/z 336 [M+H]+.

Workup

  1. customThis compound was obtained in 38% yield as a white solid

Sources & evidence

ORD record
ord-d5290a6a412746dc831adda994fab58c
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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