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Acetic Anhydride → HCID 11711523、化合物

HRID 1781992
ノート
印刷プレビュー

反応式

HRID 1781992 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

HCID 11711523HCID 11711523、化合物収率 92%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7607adb8172842e19e814c4670b1e131
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07498327B2

反応ノート

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