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Acetaldehyde → (S)-10-[4-Ethyl-3-(2-methoxyethyl)piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triazabenzo[f]azulene dihydrochloride

HRID 131501
ノート
印刷プレビュー

反応式

HRID 131501 の反応式
[CH3:1][O:2][CH2:3][CH2:4][C@@H:5]1[NH:10][CH2:9][CH2:8][N:7]([C:11]2[C:20]3[N:19]=[C:18]([CH:21]([CH3:23])[CH3:22])[S:17][C:16]=3[NH:15][C:14]3[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=3[N:12]=2)[CH2:6]1.[CH:28](=O)[CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:45]C(Cl)C>C(=O)(O)[O-].[Na+]>[ClH:45].[ClH:45].[CH2:28]([N:10]1[CH2:9][CH2:8][N:7]([C:11]2[C:20]3[N:19]=[C:18]([CH:21]([CH3:23])[CH3:22])[S:17][C:16]=3[NH:15][C:14]3[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=3[N:12]=2)[CH2:6][C@@H:5]1[CH2:4][CH2:3][O:2][CH3:1])[CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 177AcetaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 135485511(S)-10-[3-(2-Methoxyethyl)piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triazabenzo[f]azulene

生成物 1

HCID 136384261(S)-10-[4-Ethyl-3-(2-methoxyethyl)piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triazabenzo[f]azulene dihydrochloride収率 71%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

Combine (S)-10-[3-(2-methoxyethyl)piperazin-1-yl]-2-isopropyl 4H-3-thia-1,4,9-triazabenzo[f]azulene (0.103 g, 0.267 mmol), acetaldehyde (30 μL, 0.534 mmol), and sodium triacetoxyborohydride (0.085 g, 0.401 mmol) in dichloroethane (7 mL) and stir, at room temperature for 6 hours. Dilute the mixture with saturated aqueous sodium bicarbonate and extract three times with dichloromethane. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure to give the crude product. Purification by flash chromatography, eluting with a step gradient starting with dichloromethane going to 5% 2N ammonia-methanol in dichloromethane, gives the free base of the title compound (0.79 g, 71%) as a yellow foam: mass spectrum (APCI): m/z=414.2 (M+1). Isolate clean product as the corresponding dihydrochloride in the manner described in Example 319. Exact Mass, Calc: 414.2328; Found: 414.2326.

後処理

  1. extractionextract three times with dichloromethane
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. customto give the crude product
  5. customPurification by flash chromatography
  6. washeluting with a step gradient

出典と根拠

ORDレコード
ord-1065ab0a9ab341d59bf52ba1effc0311
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07384934B2

反応ノート

読み込み中…

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