Pyridine → HCID 117859737, compound

HRID 1486341Notes

Reaction equation

HRID 1486341 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]([NH2:10])[CH2:8][NH2:9])[CH:4]=[N:3]1.[F:11][C:12]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:13]=1[CH2:14][O:15][C:16]1[N:21]2[N:22]=[C:23]([CH3:28])[C:24]([C:25](Cl)=[O:26])=[C:20]2[CH:19]=[C:18]([CH3:29])[CH:17]=1.N1C=CC=CC=1>ClC(Cl)C>[NH2:10][CH:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)[CH2:8][NH:9][C:25]([C:24]1[C:23]([CH3:28])=[N:22][N:21]2[C:16]([O:15][CH2:14][C:13]3[C:30]([F:34])=[CH:31][CH:32]=[CH:33][C:12]=3[F:11])=[CH:17][C:18]([CH3:29])=[CH:19][C:20]=12)=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 435195091154875-76-9HCID 121434555HCID 121434555, compound

Product 1

HCID 117859737HCID 117859737, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

14.0 mg (0.10 mmol) of 1-(1-methyl-1H-pyrazol-4-yl)ethane-1,2-diamine were initially charged in a 96-well deep well multititre plate. A solution of 35.1 mg (0.10 mmol) of 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carbonyl chloride in 0.6 ml of dichloroethane and 0.032 ml (0.40 mmol) of pyridine were added successively and the mixture was stirred at RT overnight. Then the solvent was evaporated off completely, the residue was dissolved in 0.8 ml of DMF and filtered, and the target compound was isolated from the filtrate by preparative LC-MS (Method 9). The product-containing fractions were concentrated under reduced pressure using a centrifugal dryer. The residue of each product fraction was dissolved in 0.6 ml of DMSO. These were combined and finally freed of the solvent in a centrifugal dryer. 18 mg (37% of theory; 94% purity) of the title compound were obtained.

Workup

  1. customThen the solvent was evaporated off completely
  2. dissolutionthe residue was dissolved in 0.8 ml of DMF
  3. filtrationfiltered
  4. customthe target compound was isolated from the filtrate by preparative LC-MS (Method 9)
  5. concentrationThe product-containing fractions were concentrated under reduced pressure
  6. dissolutionThe residue of each product fraction was dissolved in 0.6 ml of DMSO

Sources & evidence

ORD record
ord-27522980d049452e8d9b63df25e5c1e0
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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