2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → tert-butyl 3-[7-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]propanoate

HRID 400785Notes

Reaction equation

HRID 400785 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].[NH2:20][C:21](=[N:41]O)[C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][N:28]([CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]2)=[CH:24][CH:23]=1>CCOC(C)=O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:20]=[C:21]([C:22]3[CH:31]=[C:30]4[C:25]([CH2:26][CH2:27][N:28]([CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]4)=[CH:24][CH:23]=3)[N:41]=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

4

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 76787417HCID 76787417, compound

Product 1

HCID 67401365tert-butyl 3-[7-{5-[2-(methoxymethyl)-2'-methylbiphenyl-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 2 starting from Intermediate 14 (154 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. 1H NMR (DMSO-d6) δ 8.32 (d, J=1.6 Hz, 1H), 8.16 (dd, J=8.0, 2.0 Hz, 1H), 7.87 (dd, J=8.0, 1.6 Hz, 1H), 7.82 (d, J=1.4 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.38-7.26 (m, 4H), 7.15 (d, J=7.2 Hz, 1H), 4.25-4.14 (m, 2H), 3.71 (s, 2H), 3.25 (s, 3H), 2.91-2.86 (m, 2H), 2.78-2.70 (m, 4H), 2.53-2.46 (m, 2H), 2.04 (s, 3H), 1.40 (s, 9H). LC/MS (method B): 540.1 (M+H)+. HPLC (Method A) Rt 4.81 min (Purity: 97.4%).

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-cf25e3bf68694a479b601c9787a8a308
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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