1,1'-Carbonyldiimidazole → Tert-butyl 3-(3-(4-fluoro-3-(imidazo[1,2-a]pyridine-3-carboxamido)phenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

HRID 570358Notes

Reaction equation

[C:1]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[N:36]O)[NH2:35])=[CH:30][C:29]=1[NH:38][C:39]([C:41]1[N:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]2=[N:43][CH:42]=1)=[O:40]>CN1C(=O)CCC1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:35]=[C:12]([CH:10]3[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:11]3)[O:14][N:36]=2)=[CH:30][C:29]=1[NH:38][C:39]([C:41]1[N:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]2=[N:43][CH:42]=1)=[O:40]

Participants

Conditions

Temperature: 125 °C

Procedure

To a stirring solution of Boc-azetidine-3-carboxylic acid (162 mg, 0.8 mmol) in anhydrous NMP (4 mL) was added CDI (131 mg, 0.8 mmol). The reaction was stirred for 10 minutes. N-(2-fluoro-5-(N′-hydroxycarbamimidoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (50) (125 mg, 0.4 mmol) was added and the reaction was stirred for 15 minutes, then heated via microwave at 125° C. for 15 minutes. The crude was purified via reverse phase HPLC to afford tert-butyl 3-(3-(4-fluoro-3-(imidazo[1,2-a]pyridine-3-carboxamido)phenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F27) as a white solid. MS m/z 479.2 (M+1)+.

Workup

stirringthe reaction was stirred for 15 minutes
customThe crude was purified via reverse phase HPLC

Sources & evidence

ORD record: ord-9adff66cc3f84eee89527831673ce04a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023839B2

Reaction notes

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