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 2112961Notes

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 (which may be produced as in Example 6) (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 water (2 mL), 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 solid that was purified by silica gel chromatography (gradient elution: 0-20% isopropanol/dichloromethane) to give the title compound as a solid. 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 solid
customthat was purified by silica gel chromatography (gradient elution: 0-20% isopropanol/dichloromethane)

Sources & evidence

ORD record: ord-353f9e3f498f48fa85039e70e5078b77
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524860B2

Reaction notes

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