Sodium Hydroxide → HCID 118364776, compound

HRID 1478595Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][CH:17]4[CH2:22][CH2:21][CH2:20][N:19]([C:23]5[N:28]=[CH:27][C:26]([C:29]6[CH2:34][CH2:33][N:32]([C:35](OC(C)(C)C)=O)[CH2:31][CH:30]=6)=[CH:25][N:24]=5)[CH2:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[OH-].[Na+]>C=O.C(O)=O>[CH3:35][N:32]1[CH2:31][CH:30]=[C:29]([C:26]2[CH:27]=[N:28][C:23]([N:19]3[CH2:20][CH2:21][CH2:22][CH:17]([CH2:16][N:13]4[C:11]5=[N:12][C:7]([C:5]6[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=6)=[CH:8][N:9]=[C:10]5[N:15]=[N:14]4)[CH2:18]3)=[N:24][CH:25]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 95 °C

Procedure

tert-butyl 4-(2-(3-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidin-1-yl)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (71 mg, 0.13 mmol) was dissolved in 35% HCHO (0.2 ml)+HCO2H (1 ml), followed by stirring at 95° C. overnight. After the completion of the reaction, the reaction mixture was adjusted to pH 11-12 with NaOH (aq.), and extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (1-((1-(5-(1-methyl-1,2,3,6-tetrahydro pyridin-4-yl)pyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (10 mg, 16%).

Workup

customAfter the completion of the reaction
extractionextracted with H2O, EA, and brine
customby drying
filtration(Na2SO4), filtration, and concentration under reduced pressure
customthe residue was purified by column chromatography (MeOH:MC=1:10)

Sources & evidence

ORD record: ord-e396328fa0ad4de88b8d7390de50a741
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403831B2

Reaction notes

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