Tetrabutylammonium Fluoride → 5-(3,5-Dicyano-2,6-dimethyl-1,4-dihydro-pyridin-4-yl)-3-(2-hydroxy-ethylamino)-indazole-1-carboxylic acid tert-butyl ester

HRID 218497Notes

Reaction equation

HRID 218497 reaction equation
[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]3[C:18]([C:27]#[N:28])=[C:19]([CH3:26])[NH:20][C:21]([CH3:25])=[C:22]3[C:23]#[N:24])=[CH:14][CH:15]=2)[C:10]([NH:29][CH2:30][CH2:31][OH:32])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 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 690419115-(3,5-Dicyano-2,6-dimethyl-1,4-dihydro-pyridin-4-yl)-3-(2-hydroxy-ethylamino)-indazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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 (6.58 g), from Synthetic Example 21, was dissolved in THF (350 mL), under Argon, and a solution of TBAF in THF (1M, 28.5 mL) was added. The mixture was stirred overnight at room temperature. The mixture was quenched with saturated ammonium chloride solution, diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried and concentrated to give crude 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydro-pyridin-4-yl)-3-(2-hydroxy-ethylamino)-indazole-1-carboxylic acid tert-butyl ester which was used in the next step without further purification.

Workup

  1. customThe mixture was quenched with saturated ammonium chloride solution
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0f562f5cda834d10b836f541fd39e708
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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