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Methanol → (S)-10-[4-(2-Fluoro-ethyl)-3-(2-methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 131505
ノート
印刷プレビュー

反応式

HRID 131505 の反応式
B.O1CCCC1.[F:7][CH2:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[N:25]=[C:24]([C:27]([F:30])([F:29])[F:28])[S:23][C:22]=3[NH:21][C:20]3[CH:31]=[CH:32][CH:33]=[CH:34][C:19]=3[N:18]=2)[CH2:13][C@@H:12]1[CH2:35][CH2:36][O:37][CH3:38])=O.CO.C(N)CN>O1CCCC1.O.ClCCl>[F:7][CH2:8][CH2:9][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[N:25]=[C:24]([C:27]([F:30])([F:29])[F:28])[S:23][C:22]=3[NH:21][C:20]3[CH:31]=[CH:32][CH:33]=[CH:34][C:19]=3[N:18]=2)[CH2:13][C@@H:12]1[CH2:35][CH2:36][O:37][CH3:38]
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

8

反応物 4

HCID 887MethanolHCID 3301EthylenediamineHCID 2723981Borane;tetrahydrofuranHCID 136090351(S)-2-Fluoro-1-[2-(2-methoxy-ethyl)-4-(2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulen-10-yl)-piperazin-1-yl]-ethanone

生成物 1

HCID 136090347(S)-10-[4-(2-Fluoro-ethyl)-3-(2-methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

試薬・触媒・溶媒

3
HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Add a solution of borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran; 3.8 mL, 3.8 mmol) to a 0° C. solution of (S)-2-fluoro-1-[2-(2-methoxy-ethyl)-4-(2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulen-10-yl)-piperazin-1-yl]-ethanone (0.18 g, 0.38 mmol) in anhydrous tetrahydrofuran (3 mL) and stir at 0° C. for 3 hours. Quench the reaction, in an ice/water bath, slowly with methanol. Concentrate the reaction under reduced pressure and reconstitute in anhydrous dichloroethane (6 mL). Add ethylenediamine (0.23 mL, 3.4 mmol) and reflux for 45 minutes. Cool the reaction to ambient temperature and dilute with deionized water and dichloromethane (20 mL each). Separate the organic layer and extract the aqueous layer with dichloromethane (2×). Wash the combined organics with deionized water and then a saturated solution of sodium chloride, and then dry (sodium sulfate), filter, and concentrate under reduced pressure to an orange oil (0.19 g). Purify the oil by flash chromatography, eluting with a gradient of a solution of ethyl acetate:hexane (1:1, 0-50% in hexane over 45 minutes, then 100% for 13 minutes) to give the title compound: 0.050 g (29%). Mass spectrum (APCI+, m/e): 458 (M+1).

後処理

  1. customQuench
  2. customthe reaction
  3. concentrationConcentrate
  4. customthe reaction under reduced pressure and reconstitute in anhydrous dichloroethane (6 mL)
  5. temperatureCool
  6. customthe reaction to ambient temperature
  7. customSeparate the organic layer
  8. extractionextract the aqueous layer with dichloromethane (2×)
  9. washWash the combined organics with deionized water
  10. dry with materiala saturated solution of sodium chloride, and then dry (sodium sulfate)
  11. filtrationfilter
  12. concentrationconcentrate under reduced pressure to an orange oil (0.19 g)
  13. customPurify the oil by flash chromatography
  14. washeluting with a gradient of a solution of ethyl acetate:hexane (1:1, 0-50% in hexane over 45 minutes

出典と根拠

ORDレコード
ord-bb4991a90cd841a788b8dd9cdf23b2e3
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

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