Water → HCID 86703429, compound

HRID 1501618Notes

Reaction equation

HRID 1501618 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:50][CH2:51][C:52]1[C:53](=[O:62])[NH:54][C:55]([CH3:61])=[CH:56][C:57]=1[CH2:58][O:59][CH3:60].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([NH:50][CH2:51][C:52]2[C:53](=[O:62])[NH:54][C:55]([CH3:61])=[CH:56][C:57]=2[CH2:58][O:59][CH3:60])=[O:16])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:12])[CH3:13])[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2724699PyBOPHCID 552557633-(aminomethyl)-4-(methoxymethyl)-6-methyl-2(1H)-PyridinoneHCID 86711273HCID 86711273, compound

Product 1

HCID 86703429HCID 86703429, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.155 g, 0.549 mmol) in DMSO (2 mL), PyBOP (0.429 g, 0.823 mmol) was added and reaction stirred at room temperature for 15 min. Then 3-(aminomethyl)-4-(methoxymethyl)-6-methylpyridin-2(1H)-one (0.1 g, 0.549 mmol) was added and reaction stirred overnight. On completion, water was added and solid that precipitates out was filtered and washed with water to obtain the desired intermediate (0.06 g, 24.5%).

Workup

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customsolid that precipitates out
  5. filtrationwas filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-d0eae0e89f4045fabd914b0703f27f95
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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