2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → Tert-butyl (2-methoxyethyl)(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)carbamate

HRID 219994Notes

Reaction equation

HRID 219994 reaction equation
[NH2:1][C:2](=[N:22][OH:23])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][N:7]([CH2:15][CH2:16][O:17][CH3:18])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[CH3:24][O:25][CH2:26][C:27]1[CH:32]=[C:31]([C:33](O)=O)[CH:30]=[CH:29][C:28]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:42]>>[CH3:18][O:17][CH2:16][CH2:15][N:7]([CH2:6][C:5]1[CH:19]=[CH:20][CH:21]=[C:3]([C:2]2[N:1]=[C:33]([C:31]3[CH:30]=[CH:29][C:28]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[CH3:42])=[C:27]([CH2:26][O:25][CH3:24])[CH:32]=3)[O:23][N:22]=2)[CH:4]=1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 72307486tert-Butyl 3-[amino(hydroxyimino)methyl]benzyl(2-methoxyethyl)carbamate

Product 1

HCID 86645661Tert-butyl (2-methoxyethyl)(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)carbamate

Procedure

The title compound was prepared following procedure described for example 141, step 1, but starting from Intermediate 70 (194.03 mg; 0.60 mmol) and Intermediate 28 (161.47 mg; 0.63 mmol), the crude mixture was purified by flash chromatography (C-hex/(DCM/EtOAc 1:1) to afford the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 8.45 (d, J=1.4 Hz, 1H), 8.17 (dd, J=7.8, 1.7 Hz, 1H), 8.11-8.08 (m, 2H), 7.48 (t, J=7.7 Hz, 1H), 7.41-7.23 (m, 5H), 7.13 (d, J=7.3 Hz, 1H), 4.63-4.60 (m, 2H), 4.23 (s, 2H), 3.54-3.33 (m, 10H), 2.08 (s, 3H), 1.49 (br s, 9H).). LC/MS (Method B): 544.5 (M+H)+. HPLC (Method A) Rt 6.61 min (Purity: 99.5%).

Workup

  1. customThe title compound was prepared following procedure
  2. customthe crude mixture was purified by flash chromatography (C-hex/(DCM/EtOAc 1:1)

Sources & evidence

ORD record
ord-e45b7475d0d442dc8a41f46cd054b0f2
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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