3-(Methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acid → Ethyl 4-(2-fluoro-4-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}phenoxy)butanoate

HRID 219986Notes

Reaction equation

HRID 219986 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:7]([OH:9])=O.[NH2:20][C:21](=[N:38]O)[C:22]1[CH:36]=[CH:35][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([F:37])[CH:23]=1>>[F:37][C:24]1[CH:23]=[C:22]([C:21]2[N:38]=[C:7]([C:6]3[CH:10]=[CH:11][C:12]([N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=3)[O:9][N:20]=2)[CH:36]=[CH:35][C:25]=1[O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

3

Reactant 2

HCID 594958043-(Methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acidHCID 72307473Ethyl 4-{4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}butanoate

Product 1

HCID 59495633Ethyl 4-(2-fluoro-4-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}phenoxy)butanoate

Procedure

The title compound was prepared following procedure described for example 141, step 1, but starting from Intermediate 58 (158 mg; 0.60 mmol) and Intermediate 66 (162.04 mg; 0.57 mmol), the crude mixture was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1) to afford the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.30 (d, J=2.1 Hz, 1H), 8.07 (dd, J=8.2, 2.0 Hz, 1H), 7.92-7.87 (m, 2H), 7.26 (d, J=8.4 Hz, 1H), 7.06 (t, J=8.5 Hz, 1H), 4.67-4.61 (m, 2H), 4.20-4.13 (m, 4H), 3.49 (s, 3H), 3.17 (br s, 1H), 3.06-3.03 (m, 1H), 2.65 (br s, 1H), 2.57 (t, J=7.3 Hz, 2H), 2.19 (quint, J=6.6 Hz, 2H), 1.86-1.70 (m, 4H), 1.51-1.48 (m, 2H), 1.27 (t, J=7.1 Hz, 3H), 0.90 (d, J=6.0 Hz, 3H). LC/MS (Method B): 512.4 (M+H)+. HPLC (Method A) Rt 4.62 min (Purity: 100.0%).

Workup

  1. customThe title compound was prepared following procedure
  2. customthe crude mixture was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1)

Sources & evidence

ORD record
ord-dbb33ef468a843d79d857d5d2d8dbe54
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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