Cesium carbonate → HCID 178433933, compound

HRID 1497930Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([NH:14][C:15]3[CH:20]=[C:19]([C:21]4[N:25]=[C:24]([CH:26]5[CH2:29][C:28]([F:31])([F:30])[CH2:27]5)[O:23][N:22]=4)[CH:18]=[CH:17][C:16]=3[F:32])=[O:13])=[CH:10][N:11]=2)[CH:8]=1)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl.[C:40](=[NH:43])([NH2:42])[CH3:41]>CS(C)=O>[F:30][C:28]1([F:31])[CH2:27][CH:26]([C:24]2[O:23][N:22]=[C:21]([C:19]3[CH:18]=[CH:17][C:16]([F:32])=[C:15]([NH:14][C:12]([C:9]4[N:7]5[CH:8]=[C:3]([C:1]6[NH:43][C:40]([CH3:41])=[N:42][N:2]=6)[CH:4]=[CH:5][C:6]5=[N:11][CH:10]=4)=[O:13])[CH:20]=3)[N:25]=2)[CH2:29]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-cyano-N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (42h) (15.0 mg, 0.034 mmol), CuBr (9.2 mg, 0.007 mmol), Cs2CO3(39 mg, 0.12 mmol), and acetimidamide hydrochloride (6.6 mg, 0.07 mmol) in DMSO (1 mL) was heated at 120° C. overnight. The reaction mixture was purified by HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-fluorophenyl)-6-(5-methyl-4H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (F61). MS m/z 495.1 (M+1)+.

Workup

customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record: ord-bcb7224af0054e3f987553de3cfaa087
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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