Dichloromethane → HCID 117957331, compound

HRID 1474434Notes

Reaction equation

HRID 1474434 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C:12]1[N:16]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:15]=[C:14]([Br:24])[CH:13]=1)=[O:11].C(Cl)Cl.Cl[C:29]([O:31][CH3:32])=[O:30]>N1C=CC=CC=1>[Br:24][C:14]1[CH:13]=[C:12]([C:10]([NH:9][C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:29](=[O:30])[O:31][CH3:32])=[O:11])[N:16]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 117949317HCID 117949317, compound

Product 1

HCID 117957331HCID 117957331, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

N-(2-amino-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide prepared in Step 2 (1.18 g, 2.91 mmol), CH2Cl2 (2 M, 1.46 mL) and pyridine (1 M, 2.91 mL) were introduced to a 50 mL round flask. The mixture thus obtained was cooled down to 0° C., added with methyl chloroformate (2.25 mL, 29.1 mmol, 10.0 eq), and refluxed at 80° C. for 15 hours. Upon completion of the reaction, the solvent was removed under reduced pressure. The residue was extracted with 1 M HCl (20 mL) and ethyl acetate (20 mL x 2), washed with brine (20 mL). The organic layer thus obtained was dried over MgSO4 and concentrated under reduced pressure. Subsequently, the residue was purified by silica gel column chromatography (EA:Hex=2:3→EA:Hex=1:1) to obtain the title compound (426.7 mg, yield: 32%).

Workup

  1. customThe mixture thus obtained
  2. temperaturerefluxed at 80° C. for 15 hours
  3. customUpon completion of the reaction
  4. customthe solvent was removed under reduced pressure
  5. extractionThe residue was extracted with 1 M HCl (20 mL) and ethyl acetate (20 mL x 2)
  6. washwashed with brine (20 mL)
  7. customThe organic layer thus obtained
  8. dry with materialwas dried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customSubsequently, the residue was purified by silica gel column chromatography (EA:Hex=2:3→EA:Hex=1:1)

Sources & evidence

ORD record
ord-c41f2f86ca674f1ab10be18937235ef8
Source dataset
uspto-grants-2015_04
Patent number
US09018233B2

Reaction notes

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