1,2-Dichloroethane → HCID 23156171, compound

HRID 1890644Notes

Reaction equation

HRID 1890644 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].C(Cl)CCl.O.ON1C2C=CC=CC=2N=N1.[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][CH:53]([C:56](O)=[O:57])[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]>C1COCC1.CN(C=O)C.O>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:56]([CH:53]4[CH2:54][CH2:55][N:50]([C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])[CH2:51][CH2:52]4)=[O:57])[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 23156153HCID 23156153, compound

Product 1

HCID 23156171HCID 23156171, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Compound 140 (0.200 g, 0.55 mmol) was dissolved in THF-DMF (1:4)(5.0 mL), and EDC (0.138 g, 0.72 mmol), 1-hydroxybenzotriazole hydrate (89.2 mg, 0.66 mmol) and 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (151 mg, 0.66 mmol) were added to the solution, followed by stirring at room temperature overnight. The reaction mixture was added with water and extracted with ethyl acetate three times. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 4-[4-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylcarbonyl]piperidine (0.311 g, 0.54 mmol, 98%).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-871a94e0f47a4638951cde6e160cf5f8
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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