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Boron tribromide dichloromethane → Ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate

HRID 2233974
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HRID 2233974 반응식
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([CH2:23][O:24]C)[N:22]=2)[CH2:14][CH2:13]1)=[O:10].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([CH2:23][OH:24])[N:22]=2)[CH2:14][CH2:13]1)=[O:10]
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참가 물질

4

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HCID 22277759Boron tribromide dichloromethaneHCID 68579848Ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-(methoxymethyl)-1,3-thiazole-5-carboxylate

생성물 1

HCID 68580870Ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate수율 41.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

Ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-(methoxymethyl)-1,3-thiazole-5-carboxylate (Example 276; 50 mg; 0.105 mmol) was dissolved in anhydrous DCM and cooled to −78° C. 1 M Boron tribromide/DCM (105 μl; 0.105 mmol) was added dropwise. The mixture was stirred at −78° C. for 15 min, then at room temperature for 4 h. The mixture was diluted with DCM, washed with water and dried over Na2SO4. Organic phase was concentrated in vacuo giving the title compound (20 mg).

후처리

  1. waitat room temperature for 4 h
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationOrganic phase was concentrated in vacuo

출처 및 근거

ORD 기록
ord-4083563f36ed43a699695bab4f572b01
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709503B2

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