Hydrochloric Acid → 1-Ethyl-3-[5-(pyrrolidine-1-carbonyl)-7-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea

HRID 2112938Notes

Reaction equation

C(O[C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8](Br)[CH:7]=1)=[O:5])C.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.Cl.C(=O)(O)[O-].[Na+]>CS(C)=O.O>[CH2:19]([NH:18][C:16]([NH:15][C:13]1[N:14]=[C:10]2[CH:9]=[C:8]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:7]=[C:6]([C:4]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:5])[N:11]2[N:12]=1)=[O:17])[CH3:20]

Participants

Conditions

Temperature: 23 °C

Procedure

To a suspension of 7-bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester prepared as in Example 16, Step 1 (0.080 g, 0.22 mmol) in dimethylsulfoxide (1 mL) was added pyrrolidine (0.2 mL). The reaction was stirred at 23° C. for 30 minutes, then 80° C. for 3 days. The reaction was then diluted with 2 volumes of water, acidified with 1N aqueous hydrogen chloride, then neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over sodium sulfate and evaporated in vacuo to give a colorless oily solid that was purified by silica gel chromatography (gradient elution: 0-20% isopropanol/dichloromethane) to give 1-ethyl-3-[5-(pyrrolidine-1-carbonyl)-7-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea MS (APCI)=372.2 [M+H]

Workup

wait80° C. for 3 days
extractionextracted with ethyl acetate (3×20 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
customevaporated in vacuo
customto give a colorless oily solid
customthat was purified by silica gel chromatography (gradient elution: 0-20% isopropanol/dichloromethane)

Sources & evidence

ORD record: ord-d2c7d374a6514235a0406aba78266815
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524860B2

Reaction notes

Loading…