Potassium Carbonate → HCID 22496124, compound

HRID 1815918Notes

Reaction equation

HRID 1815918 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][N:22]1[C:30]2[C:25](=[CH:26][C:27]([NH2:31])=[CH:28][CH:29]=2)[CH:24]=[N:23]1>C(C#N)(C)=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:31][C:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[N:22]([CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[N:23]=[CH:24]3)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178102,4-Dichloro-1,3,5-triazineHCID 219523661-(Pyridin-2-ylmethyl)-1H-indazol-5-amine

Product 1

HCID 22496124HCID 22496124, compound

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of the compound 2,4-dichloro-1,3,5-triazine (267 mg, 1.78 mmol) and solid K2CO3 (1.23 g, 8.42 mmol) was suspended in AcCN (20 mL) under nitrogen at 0° C. followed by addition of a solution of 1-pyridin-2-ylmethyl-1H-indazol-5-ylamine (Step 3) (400 mg, 1.78 mmol) in AcCN (3 mL) over 5 min. The mixture was stirred at 0° C. for 1 h. The reaction was quenched by pouring onto water. The organics were extracted into EtOAc (200 mL), washed with brine, dried over anh. Na2SO4, concentrated under reduced pressure then purified by column chromatography (elution with EtOAc followed by 9:1 CH2Cl2/MeOH) to give (4-chloro-[1,3,5]triazin-2-yl)-(1-pyridin-2-ylmethyl-1H-indazol-5-yl)-amine.

Workup

  1. customThe reaction was quenched
  2. additionby pouring onto water
  3. extractionThe organics were extracted into EtOAc (200 mL)
  4. washwashed with brine
  5. dry with materialdried over anh. Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customthen purified by column chromatography (elution with EtOAc followed by 9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-fb2bbb1982524b708d3e152f87fd7db9
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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