Morpholine → N-{5-[2-bromo-5-(morpholin-4-ylsulfonyl)-3-thienyl]-4-methyl-1,3-thiazol-2-yl}acetamide

HRID 1948445노트

반응식

HRID 1948445 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].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:19])=[O:18])=[CH:12][C:11]=1[C:7]1[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[CH3:10]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

생성물 1

HCID 86623158N-{5-[2-bromo-5-(morpholin-4-ylsulfonyl)-3-thienyl]-4-methyl-1,3-thiazol-2-yl}acetamide수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonyl chloride, prepared as in Step III of Example 23 (136 mg; 0.33 mmol; 1 eq), is dissolved in DCM (10 ml). Morpholine (0.25 ml; 1.65 mmol; 5 eq) and DIEA (0.17 ml; 0.98 mmol; 3 eq) are added under a nitrogen atmosphere. After 3 hours, 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 flash chromatography using cyclohexane/EtOAc (1/1) as eluent, affording the expected compound as an oil (118 mg; 77%).

후처리

  1. customsolvents are evaporated
  2. dissolutionThe crude product is dissolved in DCM
  3. washwashed with NH4Cl saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents, crude material
  6. customis purified by flash chromatography

출처 및 근거

ORD 기록
ord-fd1e703e57ea4a58bbea85556380ecfe
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399497B2

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