2-[(Dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylic acid → N,N-dimethyl-1-(2'-methyl-4-{3-[3-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}biphenyl-2-yl)methanamine

HRID 2410568Notes

Reaction equation

HRID 2410568 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH3:3].O[N:22]=[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=1)[NH2:24]>>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[O:13][N:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=3)[N:22]=2)[CH:8]=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

3

Reactant 2

HCID 580664082-[(Dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylic acidHCID 76685351N'-hydroxy-3-(methylsulfonyl)benzenecarboximidamide

Product 1

HCID 46940125N,N-dimethyl-1-(2'-methyl-4-{3-[3-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}biphenyl-2-yl)methanamine

Procedure

The title compound was prepared following the general procedure 3 starting from Intermediate 8 and Intermediate 19 and was isolated as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.59 (t, J=1.7 Hz, 1H), 8.47 (m, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.21 (m, 1H), 8.15 (dd, J=1.9, 7.9 Hz, 1H), 7.92 (t, J=7.9 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.35-7.26 (m, 3H), 7.11 (d, J=7.1 Hz, 1H), 3.35 (s, 3H), 3.19 (brs, 2H), 2.09 (s, 6H), 2.02 (s, 3H). LC/MS (Method B): 448.3 (M+H)+. HPLC (Method A) Rt 3.51 min (Purity: 98.5%).

Workup

  1. customwas isolated as a white powder

Sources & evidence

ORD record
ord-5adf99cb9ef2496a96b6409040a986e3
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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