HCID 59341798, compound → 1-(6-Quinolinylmethyl)-1H-1,2,3-triazolo[4,5-b]pyrazine-6-carboxylic acid

HRID 16011Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21]([O:23]C)=[O:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a suspension of the methyl 1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carboxylate (200 mg, 0.624 mmol) in THF (40 ml) cooled to 5° C. with ice bath was added potassium trimethylsilanoate (80.1 mg, 0.62 mmol). After stirring for 20 mins at 5° C., the reaction mixture was concentrated. The resulting residue was dissolved in 7 ml of DMAC and purified via reversed phase column eluted with 5-75% 0.1% TFA H2O and 0.1% TFA ACN to afford the desired product (100 mg, 66%).

Workup

concentrationthe reaction mixture was concentrated
dissolutionThe resulting residue was dissolved in 7 ml of DMAC
custompurified via reversed phase column
washeluted with 5-75% 0.1% TFA H2O and 0.1% TFA ACN

Sources & evidence

ORD record: ord-96311789161f4549b21c219c8db92ddb
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732604B2

Reaction notes

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