2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → 2-(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethanol

HRID 219995Notes

Reaction equation

HRID 219995 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].O[N:21]=[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][OH:32])[CH:25]=1)[NH2:23]>>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:23]=[C:22]([C:24]3[CH:25]=[C:26]([CH2:30][CH2:31][OH:32])[CH:27]=[CH:28][CH:29]=3)[N:21]=2)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Participants

3

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 76662611N'-hydroxy-3-(2-hydroxyethyl)benzenecarboximidamide

Product 1

HCID 594956822-(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethanol

Procedure

The title compound was obtained following procedure described for example 54 step 1 but starting from Intermediate 28 (149.42 mg; 0.58 mmol) and Intermediate 73 (100.00 mg; 0.60 mmol). Purification by column chromatography (cHex/EtOAc from 9:1 to 8:2) gave the title compound as a colorless oil. 1H NMR (DMSO-d6, 300 MHz) δ 8.32 (d, J=1.5 Hz, 1H), 8.16 (dd, J=7.9, 1.8 Hz, 1H), 7.98-7.93 (m, 2H), 7.54-7.47 (m, 2H), 7.41 (d, J=7.9 Hz, 1H), 7.36-7.26 (m, 3H), 7.15-7.13 (m, 1H), 4.71 (t, J=5.2 Hz, 1H), 4.22 (d, J=12.7 Hz, 1H), 4.16 (d, J=12.7 Hz, 1H), 3.24 (s, 3H), 2.85 (t, J=6.7 Hz, 2H), 2.03 (s, 3H). LC/MS (Method B): 401.2 (M+H)+. HPLC (Method A) Rt 5.17 min (Purity: 98.2%).

Workup

  1. customPurification by column chromatography (cHex/EtOAc from 9:1 to 8:2)

Sources & evidence

ORD record
ord-1c5fae6bdd414fa7993abae034efe5a8
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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