Methyl N-(triethylammoniosulfonyl)carbamate → 2-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-5-methyl-1,3,4-oxadiazole

HRID 588142Notes

Reaction equation

[C:1]([NH:4][NH:5][C:6]([C:8]1[C:13]2[C:14]([O:36][CH3:37])=[N:15][N:16]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]=2[CH:11]=[C:10]([Cl:38])[N:9]=1)=[O:7])(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>O1CCOCC1.C(Cl)Cl.CO>[Cl:38][C:10]1[N:9]=[C:8]([C:6]2[O:7][C:1]([CH3:2])=[N:4][N:5]=2)[C:13]2[C:14]([O:36][CH3:37])=[N:15][N:16]([C:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:12]=2[CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N′-acetyl-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide (48 mg, 0.091 mmol) was taken up in 1,4-dioxane (1.0 ml) and Burgess reagent (39.1 mg, 0.164 mmol) was added. The reaction mixture was stirred at 100° C. for 1 hour. Room temperature was attained. The reaction mixture was diluted with DCM and MeOH and was concentrated in vacuo while loading onto silica gel. The products were then purified by MPLC 0-25% EtOAc/hexanes to give 2-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-5-methyl-1,3,4-oxadiazole (43B). MS: [M+H]+ m/z 508.

Workup

customRoom temperature
concentrationwas concentrated in vacuo
customThe products were then purified by MPLC 0-25% EtOAc/hexanes

Sources & evidence

ORD record: ord-21a030b3de914d67ace9a5e12e82d90c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

Loading…