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 549965Notes

Reaction equation

HRID 549965 reaction equation
[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

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 21904192Phosphonium, (2-naphthalenylmethyl)triphenyl-, chlorideHCID 23665647Potassium tert-butoxideHCID 86631244HCID 86631244, compound

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-4f62a1435afb4745ab9157c20f556dd7
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

Loading…