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Acetic Anhydride → HCID 11711523, 화합물

HRID 1781992
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HRID 1781992 반응식
Cl.[Cl:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[S:11]([N:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][CH2:24][NH2:25])=[CH:15]1)(=[O:13])=[O:12])[CH:8]=[CH:7][S:6]2.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34].C([O-])(O)=O.[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[S:11]([N:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][CH2:24][NH:25][C:33](=[O:35])[CH3:34])=[CH:15]1)(=[O:12])=[O:13])[CH:8]=[CH:7][S:6]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 222197352-[1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl]ethylamine Hydrochloride

생성물 1

HCID 11711523HCID 11711523, 화합물수율 92%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

A stirred mixture of 2-{1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}ethylamine hydrochloride, 417 mg, 1.00 mmol) in dichloromethane and triethylamine (0.40 mL, 3.0 mmol) is treated with catalytic 4-dimethylaminopyridine (DMAP) (˜5 mg) at room temperature under nitrogen. The heterogeneous mixture is treated with acetic anhydride (0.30 mL, 3.2 mmol) and the reaction becomes homogeneous. After 16 h, the reaction is treated with saturated aqueous NaHCO3 (8 mL) for 0.3 h and then extracted with dichloromethane. The extracts are combined, dried over MgSO4 and concentrated in vacuo to a foam. The foam is treated with 20:80 ethyl acetate:hexane and concentrated in vacuo to a solid. This is triturated with ether and filtered. The filtercake is dried to afford the title product as a white solid, 389 mg (92% yield), mp 150-152° C., characterized by CHN elemental analysis and 1H NMR.

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo to a foam
  4. additionThe foam is treated with 20:80 ethyl acetate
  5. concentrationhexane and concentrated in vacuo to a solid
  6. customThis is triturated with ether
  7. filtrationfiltered
  8. customThe filtercake is dried

출처 및 근거

ORD 기록
ord-7607adb8172842e19e814c4670b1e131
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07498327B2

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