3-azetidinecarboxylic Acid → HCID 66795733, compound

HRID 2403225Notes

Reaction equation

HRID 2403225 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][O:11][CH3:12])=[C:8]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)[N:14]=2)[CH:7]=[N:6]1)[CH:2]([CH3:4])[CH3:3].[NH:26]1[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]1>>[CH2:1]([N:5]1[C:9]([CH2:10][O:11][CH3:12])=[C:8]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:25]=[CH:24][C:21]([CH2:22][N:26]4[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]4)=[CH:20][CH:19]=3)[N:14]=2)[CH:7]=[N:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 931923-azetidinecarboxylic AcidHCID 86663315HCID 86663315, compound

Product 1

HCID 66795733HCID 66795733, compound

Procedure

The title compound was prepared following the procedure described for Example 64 (step 2), but starting from 4-{5-[1-isobutyl-5-(methoxymethyl)-1H-pyrazol-4-yl]-1,2,4-oxadiazol-3-yl}benzaldehyde, obtained from step 1, (170.2 mg; 0.50 mmol) and using 3-azetidine carboxylic acid (101.1 mg; 1.0 mmol) to give Example 76 as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.14-8.11 (3 H, m), 7.56 (2 H, d, J=8.0 Hz), 4.99 (2 H, s), 4.17 (2 H, s), 4.13-4.09 (2 H, m), 4.05 (2 H, d, J=7.6 Hz), 3.97 (2 H, t, J=9.3 Hz), 3.43-3.38 (4 H, m), 2.41-2.32 (1 H, m), 0.95 (6 H, d, J=6.7 Hz). LC/MS: 426 (M+H)+. HPLC (Method A) Rt=2.32 min (Purity: 99.3%).

Workup

  1. customobtained from step 1, (170.2 mg; 0.50 mmol)

Sources & evidence

ORD record
ord-c02690dd41ac4d9f85e6cf3dc24d9599
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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