PyBOP → HCID 86703434, compound

HRID 1854082Notes

Reaction equation

HRID 1854082 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[C:10]([CH2:11][CH3:12])=[N:9][N:8]([CH:13]([CH3:15])[CH3:14])[C:6]=2[N:7]=1.[NH2:19][CH2:20][C:21]1[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([NH:19][CH2:20][C:21]2[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])=[O:18])[C:5]2[C:10]([CH2:11][CH3:12])=[N:9][N:8]([CH:13]([CH3:14])[CH3:15])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 86703433HCID 86703433, compound

Product 1

HCID 86703434HCID 86703434, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-bromo-3-ethyl-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.3 g, 0.901 mmol) and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (0.292 g, 1.92 mmol) in DMSO (4 mL) and was stirred at room temperature for 15 min. Then PyBOP (0.75 g, 1.44 mmol) was added to it and stirring was continued for 12 hr. After completion of the reaction, reaction mass was poured into ice to obtain solid, which was filtered and washed with acetonitrile followed by ether to provide the desired intermediate (0.35 g, 81.6%).

Workup

  1. customAfter completion of the reaction, reaction mass
  2. additionwas poured into ice
  3. customto obtain solid, which
  4. filtrationwas filtered
  5. washwashed with acetonitrile

Sources & evidence

ORD record
ord-bb5877ac3a8245f8b706d7468859dd4c
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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