2'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid → tert-butyl [7-{5-[2'-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]acetate

HRID 400786Notes

Reaction equation

HRID 400786 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:32]=[C:31]2[C:26]([CH2:27][CH2:28][N:29]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30]2)=[CH:25][CH:24]=1>CCOC(C)=O>[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]2[O:42][N:41]=[C:22]([C:23]3[CH:32]=[C:31]4[C:26]([CH2:27][CH2:28][N:29]([CH2:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:30]4)=[CH:25][CH:24]=3)[N:21]=2)=[CH:10][C:9]=1[C:17]([F:18])([F:20])[F:19]

Participants

4

Reactant 2

HCID 594958132'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 76787421tert-butyl [7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinolin-2(1H)-yl]acetate

Product 1

HCID 68654226tert-butyl [7-{5-[2'-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Title compound was prepared following general procedure 2 starting from Intermediate 24 (168 mg; 0.6 mmol) and Intermediate 5 (174 mg; 0.6 mmol). The reaction mixture was diluted with EtOAc, washed with water and brine and evaporated under vacuum. Purification with MD-Autoprep afforded the title compound as a yellow oil. LC/MS (method B): 550.1 (M+H)+. HPLC (Method A) Rt 4.95 min.

Workup

  1. customTitle compound was prepared
  2. washwashed with water and brine
  3. customevaporated under vacuum
  4. customPurification

Sources & evidence

ORD record
ord-68dd527c289f43ce9a6f2fd8cca623bb
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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