3-(Methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acid → HCID 66678478, compound

HRID 2410569Notes

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:39]O)[C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=1)[CH2:25][O:26][CH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([C:7]2[O:9][N:39]=[C:21]([C:22]3[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=3)[CH2:25][O:26][CH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[N:20]=2)[CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19]

Participants

Reactant 2

HCID 594958043-(Methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acid

HCID 76685331HCID 76685331, compound

Product 1

HCID 66678478HCID 66678478, compound

Procedure

Tert-butyl 3-[(3-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]propanoate was prepared following the general procedure 3 starting from Intermediate 2 and Intermediate 20. It was hydrolyzed following general procedure 8 to afford the title compound as a pale yellow powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.19 (m, 1H), 8.06 (m, 3H), 7.57 (m, 2H), 7.39 (m, 1H), 4.60 (s, 2H), 4.57 (m, 2H), 3.70 (t, J=6.2 Hz, 2H), 3.42 (s, 3H), 3.24 (m, 1H), 3.03 (m, 1H), 2.63 (m, 1H), 2.54 (t, J=6.2 Hz, 2H), 1.85-1.30 (m, 6H), 0.86 (d, J=6.1 Hz, 3H). LC/MS (Method B): 466.4 (M+H)+, 464.4 (M−H)−. HPLC (Method A) Rt 3.30 min (Purity: 98.3%).

Sources & evidence

ORD record: ord-41915c04522f4560816096848d2f9f67
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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