Triethylamine → HCID 89689816, compound

HRID 595392

Reaction equation

HRID 595392 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][N:3]=1.CCN(CC)CC.Cl[C:24](=[O:29])[C:25]([O:27][CH3:28])=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH:9][C:24](=[O:29])[C:25]([O:27][CH3:28])=[O:26])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Product 1

HCID 89689816HCID 89689816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-chloro-4-(isopropylamino)nicotinohydrazide (10) (200 mg, 0.35 mmol) in DCM (10 mL), Et3N (3.1 mmol, 3 equiv) was added and cooled to 0° C. Methyl 2-chloro-2-oxoacetate (0.42 mmol, 1.2 equiv) was added dropwise and stirred for 6 h at room temperature. The reaction mixture was quenched with aq. NaHCO3 solution and extracted in DCM. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography through silica gel and MeOH: DCM as eluent to afford methyl 2-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-2-oxoacetate.

Workup

  1. customThe reaction mixture was quenched with aq. NaHCO3 solution
  2. extractionextracted in DCM
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record
ord-c3ff1e75a7b04a05930eeca202f3e745
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Linked notes

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