Triethylamine → HCID 20627463, compound

HRID 47190Notes

Reaction equation

HRID 47190 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[C:4]([C:11]([OH:13])=O)=[CH:3]1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1.C(N(CC)CC)C>C(Cl)Cl.C(OC(=O)C)C.CN(C=O)C>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:20][C:11]([C:4]2[C:5]([C:7]([F:10])([F:9])[F:8])=[CH:6][N:2]([CH3:1])[CH:3]=2)=[O:13])=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 117887791-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylic acidHCID 21947116HCID 21947116, compound

Product 1

HCID 20627463HCID 20627463, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.54 g (2.8 mmol) 1-methyl-4-trifluoromethylpyrrole-3-carboxylic acid and 0.39 g (3.1 mmol) oxalyl chloride in 20 ml methylene chloride is stirred for 2 hours at room temperature in the presence of a catalytic amount of DMF. Then the acid chloride solution is slowly added to a solution of 0.57 g (2.8 mmol) 3-amino4-(4′-chlorophenyl)pyridine, 0.34 g (3.4 mmol) triethylamine and 15 ml methylene chloride. The resulting mixture is then stirred for 16 hours at room temperature. After the addition of ethylacetate, the organic phase is washed twice with water. After drying the organic phase over sodium sulfate, the solvent is removed in a water let vacuum. The obtained crude product is purified by column chromatography over silica gel (eluant: hexane/THF 1:3). Yield: 0.4 g 1-methyl-4-trifluoromethyl-1-1-pyrrole-3-carboxylic acid [4-(4′-chlorophenyl)pyridin-3yl]amide in the form of yellowish crystals; m.p.: 178-180° C.

Workup

  1. washthe organic phase is washed twice with water
  2. dry with materialAfter drying the organic phase over sodium sulfate
  3. customthe solvent is removed in a water
  4. customThe obtained crude product
  5. customis purified by column chromatography over silica gel (eluant: hexane/THF 1:3)

Sources & evidence

ORD record
ord-f7f961427d9648d283d0fa156689af53
Source dataset
uspto-grants-2004_03
Patent number
US06699818B1

Reaction notes

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