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Trifluoroacetic acid → (S)-N-(5-chlorobenzofuran-2-ylmethylene)-N-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]amine

HRID 856342
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HRID 856342 반응식
[CH3:1][C@@:2]1([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([NH:20][C:21](=O)OC(C)(C)C)[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.[Cl:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35](C=O)=[CH:34][C:33]=2[CH:39]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35]([CH:21]=[N:20][N:17]3[CH2:16][CH2:15][N:14]([CH2:13][C@:2]4([CH3:1])[O:6][C:5]5=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]5[CH2:3]4)[CH2:19][CH2:18]3)=[CH:34][C:33]=2[CH:39]=1
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참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 134001705-Chloro-1-benzofuran-2-carbaldehydeHCID 86760538tert-butyl(S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]carbamate

생성물 1

HCID 69480120(S)-N-(5-chlorobenzofuran-2-ylmethylene)-N-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]amine
수율 59%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of tert-butyl (S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]carbamate prepared in Example 503 (0.20 g, 0.523 mmol) and 5-chlorobenzofuran-2-carbaldehyde (0.113 g, 0.628 mmol) and methylene chloride (4 ml), trifluoroacetic acid (0.4 ml) was added followed by stirring at room temperature for 2 hours. To the reaction mixture, a saturated sodium hydrogencarbonate solution was added followed by extraction with methylene chloride. The organic phase was washed with a saturated saline solution, dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=4/1) to afford (S)-N-(5-chlorobenzofuran-2-ylmethylene)-N-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]amine (0.137 g, yield 59%) as a light yellow powder.

후처리

  1. additionwas added
  2. extractionfollowed by extraction with methylene chloride
  3. washThe organic phase was washed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe resulting filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-406a6c4b976648258569c47a5f7d2751
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262212B2

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