Triethylamine → HCID 90010275, compound

HRID 706795Notes

Reaction equation

HRID 706795 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:12])[CH:8]=[C:9]([F: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)[CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 90010382HCID 90010382, compound

Product 1

HCID 90010275HCID 90010275, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-amino-4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester (1.18 g, 6.88 mmol) in dichloromethane (14 ml) is added triethylamine (3.34 ml, 24.1 mmol). Then 4-bromobenzoyl chloride (3.02 g, 13.8 mmol) is added in portions. 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 1-(4-bromo-benzoylamino)-4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester as white solid; HPLC/MS 2.78 min (B), [M+H] 355/357.

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-989d4d0c61504177b62141591dc1dc69
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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