Pyrazole → HCID 71280718, compound

HRID 1497922Notes

Reaction equation

CS(O[CH:6]1[CH2:9][CH:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH:22][C:23]([C:25]4[N:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]5=[N:27][CH:26]=4)=[O:24])[CH:16]=3)[N:11]=2)[CH2:7]1)(=O)=O.[NH:34]1[CH:38]=[CH:37][CH:36]=[N:35]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:34]1([CH:6]2[CH2:9][CH:8]([C:10]3[O:14][N:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH:22][C:23]([C:25]5[N:29]6[CH:30]=[CH:31][CH:32]=[CH:33][C:28]6=[N:27][CH:26]=5)=[O:24])[CH:16]=4)[N:11]=3)[CH2:7]2)[CH:38]=[CH:37][CH:36]=[N:35]1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirring mixture of 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)cyclobutyl methanesulfonate (81) (25 mg, 0.0535 mmol), 1H-pyrazole (7 mg, 0.0802 mmol) and cesium carbonate (26 mg, 0.107 mmol) in anhydrous DMF (1 mL) was heated at 60° C. for 1 hour. Then, the reaction was cooled to room temperature and filtered. The crude product was purified by reverse phase preparative HPLC to give N-(5-(5-(3-(1H-pyrazol-1-yl)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F45). 1H NMR (400 MHz, d6-DMSO) δ 10.20 (s, 1H), 9.54-9.51 (m, 1H), 8.71 (s, 1H), 8.10 (dd, J=1.6, 7.2 Hz, 1H), 7.89-7.85 (m, 3H), 7.70-7.66 (m, 1H), 7.54-7.50 (m, 2H), 7.33-7.29 (m, 1H), 6.28-6.25 (m, 1H), 5.04-4.96 (m, 1H), 3.82-3.73 (m, 1H), 3.10-2.85 (m, 4), 2.37 (s, 3H). MS m/z 440.18 (M+1)+.

Workup

temperatureThen, the reaction was cooled to room temperature
filtrationfiltered
customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-91576f9696454544b860f14f104ed9b3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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