1,1'-Carbonyldiimidazole → 5-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 588152Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][NH2:11])=[O:9])[C:5]2[C:12]([O:34][CH3:35])=[N:13][N:14]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.C1N=CN([C:41](N2C=NC=C2)=[O:42])C=1>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:41](=[O:42])[NH:11][N:10]=2)[C:5]2[C:12]([O:34][CH3:35])=[N:13][N:14]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide (122 mg, 0.252 mmol) and CDI (49.1 mg, 0.303 mmol) were taken up in 1,4-dioxane (3.0 ml). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was loaded onto silica gel and purification by MPLC 0-50% EtAOc/hexanes gave 5-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-1,3,4-oxadiazol-2(3H)-one (53B). MS: [M+H]+ m/z 510.

Workup

customThe reaction mixture was loaded onto silica gel and purification by MPLC 0-50% EtAOc/hexanes

Sources & evidence

ORD record: ord-48f7414e8aa14753bb06378a1edf29e3
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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