Hydrochloric Acid → 2Chlor-3-[1-(3-chlor-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-4-cyan-5-pyrazolyl]-2-methyl-propionic acid ethyl ester

HRID 1106401Notes

Reaction equation

HRID 1106401 reaction equation
N(OC(C)(C)C)=O.[C:8]([O:13][CH2:14][CH3:15])(=[O:12])[C:9]([CH3:11])=[CH2:10].N[C:17]1[N:21]([C:22]2[C:30]([Cl:31])=[C:25]3[CH2:26][CH2:27][CH2:28][CH2:29][N:24]3[N:23]=2)[N:20]=[CH:19][C:18]=1[C:32]#[N:33].[ClH:34]>C(#N)C>[CH2:14]([O:13][C:8](=[O:12])[C:9]([Cl:34])([CH3:11])[CH2:10][C:17]1[N:21]([C:22]2[C:30]([Cl:31])=[C:25]3[CH2:26][CH2:27][CH2:28][CH2:29][N:24]3[N:23]=2)[N:20]=[CH:19][C:18]=1[C:32]#[N:33])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7343Ethyl MethacrylateHCID 10906Tert-Butyl nitriteHCID 153764335-Amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-1h-pyrazole-4-carbonitrile

Product 1

HCID 573221572Chlor-3-[1-(3-chlor-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-4-cyan-5-pyrazolyl]-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.6 g (15.5 mmol) tert-butyl nitrite, 20 ml ethyl methacrylate and 1.52 g copper-ll-chloride is added to 20 ml acetonitrile and 2.62 g (10 mmol) 5-amino-1-(3-chlor-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-4-pyrazol-carbonitrile is added in 3 portions. The mixture is stirred at room temperature for 20 hours, added to 50 ml 2N hydrochloric acid, extracted 3 times with dichloromethane, dried over magnesium sulphate and concentrated. Purification is by column chromatography using a hexane/ethyl acetate mixture.

Workup

  1. additionis added in 3 portions
  2. extractionextracted 3 times with dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-c70d98158ebb4c2fbdbff97118f3ec35
Source dataset
uspto-grants-2000_05
Patent number
US06057270

Reaction notes

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