Water → HCID 11999020, 화합물

HRID 1948450노트

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HRID 1948450 반응식
[CH2:1]([NH:4][S:5]([C:8]1[S:12][C:11](Br)=[C:10]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])[CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C([Li])CCC.O>C1COCC1>[CH2:1]([NH:4][S:5]([C:8]1[S:12][CH:11]=[C:10]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])[CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 86623160N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamideHCID 178418339Butyllithium

생성물 1

HCID 11999020HCID 11999020, 화합물수율 10%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide obtained in Step I as described above (35 mg; 0.08 mmol; 1 eq), is dissolved in dry THF (5 ml) at −70° C. under an inert atmosphere. n-Butyllithium (0.18 ml; 1 M; 0.18 mmol; 2.20 eq) is added slowly and reaction stirred at −70° C. for 1 hour before being hydrolyzed with water (0.3 ml). Reaction is warmed up to room temperature before being concentrated to dryness. Residue is taken up with water (2 ml) and EtOAc (10 ml). The organic phases are decanted, dried over MgSO4, filtrated and evaporated. Title compound is purified by reverse preparative HPLC, affording Compound (49) as a white powder (3 mg; 10%).

후처리

  1. customreaction
  2. customReaction
  3. temperatureis warmed up to room temperature
  4. concentrationbefore being concentrated to dryness
  5. customThe organic phases are decanted
  6. dry with materialdried over MgSO4
  7. filtrationfiltrated
  8. customevaporated
  9. customTitle compound is purified by reverse preparative HPLC

출처 및 근거

ORD 기록
ord-ce9274d6530945c18375dd8a8201c8ab
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399497B2

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