Citric Acid → HCID 71280931, compound

HRID 1045463Notes

Reaction equation

HRID 1045463 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:29])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.[CH3:30][O:31][C:32](Cl)=[O:33].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[N:22]1[CH:21]=[C:20]([C:18]([NH:17][C:15]2[CH:16]=[C:11]([C:8]3[N:7]=[C:6]([CH:4]4[CH2:3][N:2]([C:32]([O:31][CH3:30])=[O:33])[CH2:5]4)[O:10][N:9]=3)[CH:12]=[CH:13][C:14]=2[CH3:29])=[O:19])[N:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=12

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6586Methyl chloroformateHCID 71281043HCID 71281043, compound

Product 1

HCID 71280931HCID 71280931, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of N-(5-(5-(azetidin-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (21) (25 mg, 0.0667 mmol) in anhydrous pyridine (1 mL) was added methylchloroformate (5 μL, 0.667 mmol). The reaction was stirred to room temperature for 10 minutes. The pH was adjusted to neutral with 10% citric acid. The crude was purified by reverse phase HPLC to afford methyl 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F15) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s 1H), 9.52 (d, J=7.2 Hz, 1H), 8.71 (s, 1H), 8.10 (s, 1H), 7.82-7.91 (m, 2H), 7.69 (t, J=8.0 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.31 (td, J=7.2, 0.8 Hz, 1H), 4.15-4.44 (m, 5H) 3.59 (s, 3H), 2.37 (s, 3H). MS m/z 433.3 (M+1)+.

Workup

  1. customThe crude was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c9fc241037f64903817be3ecde02a423
Source dataset
uspto-grants-2013_10
Patent number
US08569283B2

Reaction notes

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