Hydrochloric Acid → HCID 67158816, compound

HRID 549256Notes

Reaction equation

HRID 549256 reaction equation
[ClH:1].[Br:2][C:3]1[C:7]([C:8]#[N:9])=[N:6][N:5]([CH2:10][CH2:11][CH3:12])[C:4]=1[CH2:13][C:14]1([F:27])[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1>C(O)C>[ClH:1].[Br:2][C:3]1[C:7]([C:8]#[N:9])=[N:6][N:5]([CH2:10][CH2:11][CH3:12])[C:4]=1[CH2:13][C:14]1([F:27])[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67157731HCID 67157731, compound

Product 1

HCID 67158816HCID 67158816, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrochloric acid (3.9 mL of 6 M) was added to a solution of tert-butyl 4-[(4-bromo-5-cyano-2-propyl-2H-pyrazol-3-yl)methyl]-4-fluoropiperidine-1-carboxylate (3.34 g, 7.78 mmol) in ethanol (40 mL), and the reaction was heated at 70° C. for 1.5 hours, allowed to cool to room temperature, and concentrated under reduced pressure to provide 2.9 g of 4-bromo-5-[(4-fluoropiperidin-4-yl)methyl]-1-propyl-1H-pyrazole-3-carbonitrile hydrochloride. The salt was suspended in dichloromethane (40 mL), and triethylamine (4.9 mL, 4.5 eq.) was added. The mixture was stirred for ten minutes to provide a 0.2 M solution of 4-bromo-5-[(4-fluoropiperidin-4-yl)methyl]-1-propyl-1H-pyrazole-3-carbonitrile.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33c77aa0a99747c2b2183c069f45bc9a
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

Loading…