Potassium Iodide → HCID 67976139, compound

HRID 2046221Notes

Reaction equation

HRID 2046221 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C@H:3]([NH2:5])[CH3:4].[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH2:26][CH2:27]Br)[N:15]=[C:16]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)=[O:12])[CH3:9].[I-].[K+].CC(C)([O-])C.[Na+]>C(#N)C.CN(C=O)C>[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH2:26][CH2:27][NH:5][C@H:3]([CH3:4])[C:2]([CH3:7])([CH3:6])[CH3:1])[N:15]=[C:16]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:17]=1)=[O:12])[CH3:9].[O:19]([CH2:18][C:16]1[CH:17]=[C:13]([C:11]([OH:12])=[O:10])[N:14]([CH2:26][CH2:27][NH:5][C@H:3]([CH3:4])[C:2]([CH3:7])([CH3:6])[CH3:1])[N:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 5324845(R)-3,3-Dimethyl-2-aminobutaneHCID 23676156Sodium t-butoxideHCID 67974304ethyl 1-(2-bromoethyl)-3-(phenoxymethyl)-1H-pyrazole-5-carboxylate

Product 2

HCID 67976139HCID 67976139, compoundYield 233.7%HCID 67991632HCID 67991632, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

(R)-3,3-Dimethyl-2-aminobutane (0.37 g, 2.86 mmol) was added to a suspension of 2-(2-bromoethyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.1 g, 0.28 mmol) and potassium iodide (9 mg, 0.056 mmol) in ACN (1 mL). The mixture was stirred at 90° C. for 20 hours. Sodium tert-butoxide (41 mg, 0.42 mmol) and DMF (1 mL) was added and the mixture was stirred at 130° C. for 20 minutes under microwave irradiation. The solvent was evaporated in vacuo. The crude product was washed with a 2N solution of HCl until pH 1 and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield a 1:1 mixture (R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid ethyl ester and (R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid (113 mg, 57%) as a yellow oil which was used in the next step without any further purification.

Workup

  1. stirringthe mixture was stirred at 130° C. for 20 minutes under microwave irradiation
  2. customThe solvent was evaporated in vacuo
  3. washThe crude product was washed with a 2N solution of HCl until pH 1
  4. extractionextracted with AcOEt
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-4e3feca790eb4caa95c275f0a27d50b1
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

Loading…