Pyridine → Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester

HRID 1921249노트

반응식

HRID 1921249 반응식
[F:1][C:2]1[C:7]2[S:8][CH2:9][CH:10]([NH:11][C:12]([NH:14][CH2:15][CH2:16][OH:17])=[S:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:7]2[S:8][CH2:9][CH:10]([NH:11][C:12](=[S:13])[NH:14][CH2:15][CH2:16][O:17][C:24](=[O:26])[CH3:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 25135276HCID 25135276, 화합물

생성물 1

HCID 25134381Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester수율 54.8%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(7-Fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)-3-(2-hydroxy-ethyl)-thiourea (200 mg, 0.73 mmol), pyridine (0.07 mL, 0.88 mmol) and DMAP (20 mg, 0.16 mmol) in THF (5 mL) was added a solution of acetyl chloride (0.06 mL, 0.81 mmol) in THF (2 mL) and the reaction mixture stirred for 16 h. The mixture was diluted with ethyl acetate (20 mL) and extracted with water (4 times). The organic phase was dried over Na2SO4, solvents evaporated and the residue purified by column chromatography to yield Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester (125 mg, 0.40 mmol, 54%).

후처리

  1. extractionextracted with water (4 times)
  2. dry with materialThe organic phase was dried over Na2SO4, solvents
  3. customevaporated
  4. customthe residue purified by column chromatography

출처 및 근거

ORD 기록
ord-216c90bd23c54ded9c113afac5dc9ad8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173675B2

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