Diisopropylethylamine → 5-Chloro-N-(2,4-dimethoxybenzyl)-N-{[1-(4-iodophenyl)-3-phenyl-1H-pyrazol-4-yl]methyl}-thiophene-2-carboxamide

HRID 2383354Notes

Reaction equation

HRID 2383354 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](Cl)=[O:8])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH2:20][NH:21][CH2:22][C:23]1[C:24]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:25][N:26]([C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][CH:29]=2)[CH:27]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([N:21]([CH2:20][C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[O:11][CH3:10])[CH2:22][C:23]2[C:24]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[N:25][N:26]([C:28]3[CH:33]=[CH:32][C:31]([I:34])=[CH:30][CH:29]=3)[CH:27]=2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 581121691-(2,4-Dimethoxyphenyl)-N-{[1-(4-iodophenyl)-3-phenyl-1H-pyrazol-4-yl]methyl}methanamine

Product 1

HCID 574369265-Chloro-N-(2,4-dimethoxybenzyl)-N-{[1-(4-iodophenyl)-3-phenyl-1H-pyrazol-4-yl]methyl}-thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 651 mg (3.597 mmol) of 5-chlorothiophene-2-carbonyl chloride in 10 ml of anhydrous tetrahydrofuran is added to a solution of 1.89 g (3.597 mmol) of the product from Example 3A and 1.25 ml of diisopropylethylamine (Hünig-Base) in 40 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours. The solvent is then removed on a rotary evaporator, and the residue is taken up in dichloromethane and washed successively with saturated sodium bicarbonate solution and water. After drying over anhydrous sodium sulphate, the mixture is filtered, evaporated and the residue is purified by preparative HPLC (Method 7). This gives 1.05 g (43% of theory) of the title compound.

Workup

  1. customThe solvent is then removed on a rotary evaporator
  2. washwashed successively with saturated sodium bicarbonate solution and water
  3. dry with materialAfter drying over anhydrous sodium sulphate
  4. filtrationthe mixture is filtered
  5. customevaporated
  6. customthe residue is purified by preparative HPLC (Method 7)

Sources & evidence

ORD record
ord-1142fb9a26dc4868a8a22c4e59d51737
Source dataset
uspto-grants-2012_09
Patent number
US08263624B2

Reaction notes

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