Acetic Acid → 1-((6-(5-Benzylbenzofuran-2-yl)-2-methylpyridin-3-yl)methyl)azetidine-3-carboxylic acid

HRID 2075272Notes

Reaction equation

[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[C:18]([CH3:24])[N:17]=3)=[CH:13][C:12]=2[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]1.C(O)(=O)C.[Na]>CO.Cl.CCOCC>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[N:17]=[C:18]([CH3:24])[C:19]([CH2:20][N:26]4[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]4)=[CH:22][CH:23]=3)=[CH:13][C:12]=2[CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 24 °C

Procedure

A suspension of 6-(5-benzylbenzofuran-2-yl)-2-methylnicotinaldehyde (160 mg, 489 μmol) and 3-azetidinecarboxylic acid (49.4 mg, 489 μmol) in MeOH (8 mL) and glacial acetic acid (44.0 mg, 733 μmol) was stirred at 24° C. for 1 h, treated with sodium borocyanohydride (15.4 mg, 244 μmol), and stirred for 2 h. The mixture was diluted with 30 mL of 1M HCl in Et2O and evaporated. Purification of the residue by RP-HPLC to give title compound as an off-white solid [hS1P1 EC50=420 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.72 (s, 2H), 7.55-7.53 (m, 2H), 7.43 (s, 1H), 7.28-7.18 (m, 6H), 4.04 (s, 2H), 3.59 (s, 2H), 3.45-3.23 (m, 8H). MS (ESI) m/z: Calculated: 412.5; Observed: 413.3 (M++1).

Workup

stirringstirred for 2 h
customevaporated
customPurification of the residue by RP-HPLC

Sources & evidence

ORD record: ord-57ad4ef949e2449cbefc24a9ff5b70af
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919519B2

Reaction notes

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