Triethylamine → HCID 90009951, compound

HRID 706793Notes

Reaction equation

HRID 706793 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:12])[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[Br:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH:12][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([Br:20])=[CH:22][CH:23]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 70280903HCID 70280903, compound

Product 1

HCID 90009951HCID 90009951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (310 mg, 1.83 mmol) in dichloromethane (4 ml) is added triethylamine (887 μl, 6.40 mmol). Then a solution of 4-bromobenzoyl chloride (803 mg, 3.66 mmol) in dichloromethane (2 ml) is added slowly. The reaction mixture is stirred for 18 hours at room temperature. The reaction mixture is partitioned between water and dichloromethane. The organic layer is washed with 1 N HCl, dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 2-(4-bromo-benzoylamino)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester as brown oil; HPLC/MS 2.10 min (A), [M+H] 352/354.

Workup

  1. customThe reaction mixture is partitioned between water and dichloromethane
  2. washThe organic layer is washed with 1 N HCl
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-623c7943df614f88b2cb520f988ed1f1
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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