Allylamine → N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 1948449ノート

反応式

HRID 1948449 の反応式
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[S:14][C:15]=2[Br:16])=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH2:21]([NH2:24])[CH:22]=[CH2:23].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:21]([NH:24][S:17]([C:13]1[S:14][C:15]([Br:16])=[C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])[CH:12]=1)(=[O:19])=[O:18])[CH:22]=[CH2:23]

参加物

5

反応物 3

HCID 7853AllylamineHCID 81531DiisopropylethylamineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

生成物 1

HCID 86623160N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride, prepared as in Step III of Example 23 (100 mg; 0.229 mmol; 1 eq) is dissolved in DCM (10 ml). Allyl amine (0.15 ml; 1.14 mmol; 5 eq) and DIEA (0.17 ml; 0.70 mmol; 3 eq) are added under a nitrogen atmosphere. After 2 hours reaction, solvents are evaporated. The crude product is dissolved in DCM and washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is purified by reverse preparative HPLC, affording N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide as a white solid (35 mg; 35%).

後処理

  1. customAfter 2 hours reaction, solvents
  2. customare evaporated
  3. dissolutionThe crude product is dissolved in DCM
  4. washwashed with NH4Cl saturated solution, water
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvents, crude material
  7. customis purified by reverse preparative HPLC

出典と根拠

ORDレコード
ord-3cb4fe89109043658f923915384380e6
出典データセット
uspto-grants-2013_03
特許番号
US08399497B2

反応ノート

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