Hydrochloric Acid → 1,4-dihydro-4-[3-[(2-hydroxyethyl)amino]-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrile

HRID 218496Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]3[C:22]([C:23]#[N:24])=[C:21]([CH3:25])[NH:20][C:19]([CH3:26])=[C:18]3[C:27]#[N:28])=[CH:14][CH:15]=2)[C:10]([NH:29][CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)=[N:9]1)=O)(C)(C)C.Cl>>[OH:32][CH2:31][CH2:30][NH:29][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([CH:17]3[C:22]([C:23]#[N:24])=[C:21]([CH3:25])[NH:20][C:19]([CH3:26])=[C:18]3[C:27]#[N:28])[CH:12]=2)[NH:8][N:9]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 690441213-[2-(Tert-butyl-dimethyl-silanyloxy)-ethylamino]-5-(3,5-dicyano-2,6-dimethyl-1,4-dihydro-pyridin-4-yl)-indazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 249602041,4-dihydro-4-[3-[(2-hydroxyethyl)amino]-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrileYield 65.6%

Procedure

A mixture of crude 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-5-(3,5-dicyano-2,6-dimethyl-1,4-dihydro-pyridin-4-yl)-indazole-1-carboxylic acid tert-butyl ester (165 mg) and HCl (4M solution in THF, 2 mL) was stirred overnight at room temperature. The mixture was partitioned between dilute aqueous sodium hydrogen carbonate solution (0.5%, 40 mL) and EtOAc (40 mL). The organic extract was dried (Na2SO4), concentrated and the residue purified by chromatography on silica gel to give 1,4-dihydro-4-[3-[(2-hydroxyethyl)amino]-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrile (66 mg) (Cpd. No. 118, Table 2).

Workup

customThe mixture was partitioned between dilute aqueous sodium hydrogen carbonate solution (0.5%, 40 mL) and EtOAc (40 mL)
extractionThe organic extract
dry with materialwas dried (Na2SO4)
concentrationconcentrated
customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record: ord-59c110c479834f6ea7e1d1092ccbfdd0
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198456B2

Reaction notes

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