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 549965노트

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HRID 549965 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-4f62a1435afb4745ab9157c20f556dd7
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943774B2

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