Triethylamine → {4-[({[1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-yl]carbonyl}amino)methyl]phenyl}boronic acid

HRID 562113Notes

Reaction equation

HRID 562113 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.[CH3:12][C:13]([N:16]1[C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]([CH3:24])=[N:17]1)([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C>[CH3:15][C:13]([N:16]1[C:20]([C:21]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([B:9]([OH:11])[OH:10])=[CH:7][CH:8]=2)=[O:22])=[CH:19][C:18]([CH3:24])=[N:17]1)([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734312(4-(Aminomethyl)phenyl)boronic acidHCID 27993401-tert-Butyl-3-methyl-1H-pyrazole-5-carbonyl chloride

Product 1

HCID 66723191{4-[({[1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-yl]carbonyl}amino)methyl]phenyl}boronic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [4-(aminomethyl)phenyl]boronic acid (145 mg, 0.966 mmol) in DMF (2 mL) was added 1-(1,1-dimethylethyl)-3-methyl-1H-pyrazole-5-carbonyl chloride (290 mg, 1.45 mmol) and triethylamine (403 μL, 2.90 mmol). The reaction was stirred for 2 h. It was then quenched and partitioned between EtOAc and H2O and the organic layer was concentrated to give {4-[({[1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-yl]carbonyl}amino)methyl]phenyl}boronic acid.

Workup

  1. customIt was then quenched
  2. custompartitioned between EtOAc and H2O
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-c852f3348bd64c5cb6263fb886c0a836
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

Loading…