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Toluene → HCID 136005564、化合物

HRID 1350428
ノート
印刷プレビュー

反応式

HRID 1350428 の反応式
[C:1]1([CH2:11][CH2:12][C@H:13]2[CH2:18][NH:17][CH2:16][CH2:15][NH:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1[S:29][C:28]2[NH:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]=[C:23](N)[C:22]=2[CH:21]=1.C1(C)C=CC=CC=1.C(N(C(C)C)C(C)C)C>C(OCC)(=O)C.O.C(O)(=O)C.CS(C)=O>[CH3:19][C:20]1[S:29][C:28]2[NH:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]=[C:23]([N:17]3[CH2:16][CH2:15][NH:14][C@@H:13]([CH2:12][CH2:11][C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[CH2:18]3)[C:22]=2[CH:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 58860672HCID 58860672、化合物HCID 135446208Olanzamine

生成物 1

HCID 136005564HCID 136005564、化合物収率 5%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒
HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
105 °C

実験手順

Combine (S)-2-(2-naphthalen-1-yl-ethyl)-piperazine (686 mg, 2.85 mmol), 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine (654 mg, 2.85 mmol), toluene (5.7 mL), DMSO (1.4 mL) and glacial acetic acid (0.5 mL). Add N-ethyldiisopropylamine (2.0 mL). Heat at 105° C. After 48 h, cool to ambient temperature and dilute with ethyl acetate and water. Extract with ethyl acetate. Wash the extracts with water and brine, dry over sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (0.5%–5%) as the eluent to give 183 mg. Purify again by radial silica gel chromatography using a 2 mm plate and 2N ammonia in methanol-methylene chloride (1%–2%) as the eluent to give 60 mg (5%) of the title compound: mass spectrum (ion spray): m/z=453 (M+1), 451 (M−1). Analysis calculated for C28H28N4S.0.2H2O: C, 73.71; H, 6.27; N, 12.28. Found: C, 73.37; H, 6.19; N, 12.00.

後処理

  1. temperaturecool to ambient temperature
  2. extractionExtract with ethyl acetate
  3. washWash the extracts with water and brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate the filtrate
  7. customPurify by silica gel chromatography
  8. customto give 183 mg
  9. customPurify again by radial silica gel chromatography

出典と根拠

ORDレコード
ord-cfca0f2850d64d90851acc099a161228
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07214673B2

反応ノート

読み込み中…

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