Citric Acid → HCID 71280931, compound

HRID 570355Notes

Reaction equation

HRID 570355 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-f778e0c4650844ccaac2378b0f1e52c5
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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