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

HRID 400787Notes

Reaction equation

HRID 400787 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]([OH:16])=O)=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].[NH2:21][C:22](=[N:42]O)[C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH2:28][N:29]([CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[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:16][N:21]=[C:22]([C:23]3[CH:32]=[C:31]4[C:26]([CH2:27][CH2:28][N:29]([CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]4)=[CH:25][CH:24]=3)[N:42]=2)=[CH:10][C:9]=1[C:17]([F:20])([F:18])[F:19]

Participants

4

Reactant 2

HCID 594958132'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 76787417HCID 76787417, compound

Product 1

HCID 67400005tert-butyl 3-[7-{5-[2'-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]propanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Title compound was prepared following general procedure 3 starting from Intermediate 24 (168 mg; 0.6 mmol) and Intermediate 25 (182 mg; 0.6 mmol). The reaction mixture was diluted with EtOAc, washed with water and brine and evaporated under vacuum. Purification by silica column chromatography (c-Hex/(DCM/EtOAc 1:1), 90/10 to 50/50) afforded the title compound as a yellow oil. LC/MS (method B): 565.2 (M+H)+. HPLC (Method A) Rt 5.00 min (Purity: 95.4%).

Workup

  1. customTitle compound was prepared
  2. washwashed with water and brine
  3. customevaporated under vacuum
  4. customPurification by silica column chromatography (c-Hex/(DCM/EtOAc 1:1), 90/10 to 50/50)

Sources & evidence

ORD record
ord-2c5b5ba3e8224871a5b1980e630340d0
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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