Triethylamine → HCID 67959040, compound

HRID 707638Notes

Reaction equation

HRID 707638 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:7]1[CH:11]=[N:10][N:9]=[C:8]1[CH2:12][CH2:13]O.CS(Cl)(=O)=[O:17].C(N(CC)CC)C>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:12]([C:8]1[O:7][CH:11]=[N:10][N:9]=1)([OH:17])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131733708HCID 131733708, compound

Product 1

HCID 67959040HCID 67959040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As per scheme-9, 2-picolinic acid hydrazide (9-a) is reacted with pyruvic acid chloride in the presence of organic base such as triethylamine in dichloromethane at a temperature 0° C. to 5° C. for up to 3 hr. The reaction mixture is further treated with p-toluene sulfonyl chloride and is allowed to stir at ambient temperature for up to 16 hr to provide pyridine-1,3,4-oxadiazole compound 9-b. The compound 9-b, thus obtained, is reacted with reducing agent sodium borohydride in methanol or ethanol at a temperature 35° C. to provide pyridine-1,3,4-oxadiazole ethanol (9-c). The compound 9-c is reacted with methanesulfonylchloride in the presence of triethylamine in dichloromethane at a temperature ranging from 0° C. to 15° C. to provide corresponding methanesulfonyl ester of pyridinyl-1,3,4-oxadiazolyl-ethanol, which is converted to corresponding pyridine-1,3,4-oxadiazolyl ethyl bromide (9-d) by treating sulfonyl ester with lithium bromide in acetone at reflux temperature.

Workup

  1. customranging from 0° C. to 15° C.

Sources & evidence

ORD record
ord-bcbd8d9485ff4b678c254188d4e9b231
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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