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

HRID 1948449노트

반응식

HRID 1948449 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3cb4fe89109043658f923915384380e6
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399497B2

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