Ammonium Chloride → 2-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(Z)-2-(2-naphthyl)vinyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

HRID 549965ノート

反応式

HRID 549965 の反応式
[Cl-].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:38][C:39]1[N:43]([CH2:44][C:45]([N:47]2[CH2:52][CH2:51][CH:50]([C:53]3[S:54][CH:55]=[C:56]([CH:58]=O)[N:57]=3)[CH2:49][CH2:48]2)=[O:46])[N:42]=[C:41]([C:60]([F:63])([F:62])[F:61])[CH:40]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:38][C:39]1[N:43]([CH2:44][C:45]([N:47]2[CH2:52][CH2:51][CH:50]([C:53]3[S:54][CH:55]=[C:56](/[CH:58]=[CH:12]\[C:3]4[CH:4]=[CH:5][C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH:2]=4)[N:57]=3)[CH2:49][CH2:48]2)=[O:46])[N:42]=[C:41]([C:60]([F:63])([F:62])[F:61])[CH:40]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 21904192Phosphonium, (2-naphthalenylmethyl)triphenyl-, chlorideHCID 23665647Potassium tert-butoxideHCID 866312444-(4-formyl-2-thiazolyl)-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine

生成物 1

HCID 671564202-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(Z)-2-(2-naphthyl)vinyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

(2-Naphthylmethyl)(triphenyl)phosphonium chloride (454 mg) is dissolved in 5 ml of tetrahydrofuran and cooled to 0° C. under argon, and potassium tert.-butoxide (125 mg) is added, whereupon the colour of the solution turns to dark red. After 10 min of stirring, 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde (200 mg) is added. The mixture is stirred at 0° C. for another 30 min and then slowly warmed to room temperature. After a further 20 min, saturated ammonium chloride solution is added, and the aqueous phase is separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(Z)-2-(2-naphthyl)vinyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (260 mg).

後処理

  1. stirringThe mixture is stirred at 0° C. for another 30 min
  2. temperatureslowly warmed to room temperature
  3. waitAfter a further 20 min
  4. customthe aqueous phase is separated off
  5. extractionAfter extraction of the aqueous phase with ethyl acetate
  6. dry with materialthe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customAfter chromatographic purification

出典と根拠

ORDレコード
ord-4f62a1435afb4745ab9157c20f556dd7
出典データセット
uspto-grants-2011_05
特許番号
US07943774B2

反応ノート

読み込み中…