2'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid → HCID 66677738, compound

HRID 2404360Notes

Reaction equation

HRID 2404360 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)=O)=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].[NH2:21][C:22](=[N:41][OH:42])[C:23]1[CH:24]=[CH:25][C:26]([Cl:40])=[C:27]([CH:39]=1)[CH2:28][N:29]([CH3:38])[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>>[Cl:40][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[N:21]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])=[C:9]([C:17]([F:18])([F:20])[F:19])[CH:10]=3)[O:42][N:41]=2)=[CH:39][C:27]=1[CH2:28][N:29]([CH3:38])[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].[ClH:40].[Cl:40][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[N:21]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])=[C:9]([C:17]([F:18])([F:20])[F:19])[CH:10]=3)[O:42][N:41]=2)=[CH:39][C:27]=1[CH2:28][N:29]([CH3:38])[CH2:30][C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 594958132'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 76685374HCID 76685374, compound

Product 2

HCID 66677738HCID 66677738, compoundHCID 131731759HCID 131731759, compound

Procedure

Tert-butyl N-(2-chloro-5-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate was prepared following the general procedure 3 starting from Intermediate 5 and Intermediate 60. It was hydrolyzed following general procedure 8 to afford the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.53 (m, 3H), 8.22 (m, 2H), 7.84 (d, J=8.3 Hz, 1H), 7.69 (d, J=8.0 Hz, 1H), 7.43-7.33 (m, 2H), 7.29 (m, 1H), 7.17 (m, 1H), 4.59 (m, 2H), 4.17 (m, 2H), 2.81 (s, 3H), 2.02 (s, 3H). LC/MS (Method B): 516.0 (M+H)+, 514.1 (M−H)−. HPLC (Method A) Rt 4.39 min (Purity: 99.6%).

Sources & evidence

ORD record
ord-eb51ccae0c414dad8b9916c6e81d2848
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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