Potassium Carbonate → HCID 136246513, compound

HRID 1482935Notes

Reaction equation

HRID 1482935 reaction equation
C(O)=O.[NH2:4][C:5]1[C:10]([OH:11])=[CH:9][N:8]=[C:7]([C:12]2[C:13]3[CH2:27][CH2:26][CH2:25][C:14]=3[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:16]=2)[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[C:36]1[C:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:40][N:39]=[CH:38][CH:37]=1>CN(C=O)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:15]1[C:14]2[CH2:25][CH2:26][CH2:27][C:13]=2[C:12]([C:7]2[N:6]=[C:5]([NH:4][C:36]3[C:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:40][N:39]=[CH:38][CH:37]=3)[C:10]([OH:11])=[CH:9][N:8]=2)=[N:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 45489794Ethyl 4-chloropyridine-3-carboxylate--hydrogen chloride (1/1)HCID 136987100HCID 136987100, compound

Product 1

HCID 136246513HCID 136246513, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3.00 g of formic acid—4-amino-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]pyrimidin-5-ol (1:1) 1-8-1 (9.22 mmol, 1.00 eq.) were dissolved in 300 mL DMF, 6.37 g potassium carbonate (46.1 mmol, 5.00 eq) were added and under nitrogen atmosphere 2.05 g ethyl 4-chloronicotinate hydrochloride (1:1) (9.22 mmol, 1.00 eq.) were added. The reaction mixture was stirred at 50° C. over night, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography twice to provide 100 mg (0.21 mmol, 2.2%) of analytically pure target compound.

Workup

  1. additionwere added
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography twice
  5. customto provide 100 mg (0.21 mmol, 2.2%) of analytically pure target compound

Sources & evidence

ORD record
ord-12c3703a2a69467aaa658a9f9a73446f
Source dataset
uspto-grants-2016_08
Patent number
US09416125B2

Reaction notes

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