4-Methylmorpholine → 2-Pyridin-4-yl-1-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}ethanone

HRID 2090596Notes

Reaction equation

HRID 2090596 reaction equation
Br.[CH3:2][C:3]1([CH3:26])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2.[N:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](O)=[O:35])=[CH:29][CH:28]=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+]>C1COCC1>[N:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([N:23]2[CH2:24][CH2:25][CH:20]([C:17]3[S:18][CH:19]=[C:15]([C:7]4[CH:6]=[CH:5][C:4]5[C:3]([CH3:26])([CH3:2])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]=5[CH:8]=4)[N:16]=3)[CH2:21][CH2:22]2)=[O:35])=[CH:29][CH:28]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 342284-Pyridineacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671662304-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide

Product 1

HCID 582464742-Pyridin-4-yl-1-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.46 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide, 81 mg (0.46 mmol) of pyridin-4-ylacetic acid, 202 μl (1.84 mmol) of 4-methylmorpholine, 361 mg (1.84 mmol) of EDCl and 135 mg (0.73 mmol) of HOBt are dissolved in 10 ml of THF and stirred at room temperature for 24 h. The reaction mixture is added to saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is separated off, dried over sodium sulfate and evaporated to dryness. The crude mixture is purified by column chromatography on silica gel.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude mixture is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2fed1cc67a9a4b73a7b90901e8534fb3
Source dataset
uspto-grants-2013_05
Patent number
US08436186B2

Reaction notes

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