Hydrochloric Acid → HCID 178428423, compound

HRID 218492Notes

Reaction equation

HRID 218492 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])[N:20]([CH3:26])[C:19]([CH3:27])=[C:18]3[C:28]#[N:29])=[CH:14][CH:15]=2)[C:10]([CH3:30])=[N:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH3:26][N:20]1[C:21]([CH3:25])=[C:22]([C:23]#[N:24])[CH:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][N:9]=[C:10]3[CH3:30])[C:18]([C:28]#[N:29])=[C:19]1[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69271935HCID 69271935, compound

Product 1

HCID 178428423HCID 178428423, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

10.56 g (26.17 mmol) 5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydro-pyridin-4-yl)-3-methyl-indazole-1-carboxylic acid tert-butyl ester, from Synthetic Example 16, were dissolved in 70 mL dioxane. 350 mL of a 4 M solution of hydrochloric acid in dioxane was added. The mixture was stirred for 2 hours and then concentrated under vacuum. The residue was dissolved in ethyl acetate, washed with saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. Purification with column chromatography gave 1,4-dihydro-1,2,6-trimethyl-4-(3-methyl-1H-indazol-5-yl)-3,5-pyridinedicarbonitrile (5.46 g, 68.8%). (Cpd. No. 306, Table 7). 1H-NMR (DMSO-D6): δ=12.67 (br s, 1H), 7.50 (s, 1H), 7.48 (d, 1H), 7.26 (d, 1H), 4.44 (s, 1H), 3.21 (s, 3H), 2.48 (s, 3H), 2.24 (s, 6H) ppm. MS (ES+): 304.45 (M++1, 100%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customPurification with column chromatography

Sources & evidence

ORD record
ord-bd9235b6e1a0478aa3fa2f104f4d82be
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

Loading…