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

HRID 2383354노트

반응식

HRID 2383354 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1142fb9a26dc4868a8a22c4e59d51737
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263624B2

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