Triethylamine → HCID 68524472, compound

HRID 1932546Notes

Reaction equation

HRID 1932546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][CH:29]([CH2:32][C:33]([OH:35])=O)[CH2:28][CH2:27]4)=[CH:22][C:21]=3[CH3:36])=[N:17][CH:18]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:37]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:37]([N:44]1[CH2:49][CH2:48][N:47]([C:33](=[O:35])[CH2:32][CH:29]2[CH2:28][CH2:27][N:26]([C:23]3[CH:24]=[CH:25][C:20]([O:19][C:16]4[N:17]=[CH:18][C:13]([NH:12][S:9]([C:4]5[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=5)(=[O:10])=[O:11])=[CH:14][CH:15]=4)=[C:21]([CH3:36])[CH:22]=3)[CH2:31][CH2:30]2)[CH2:46][CH2:45]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 68527032HCID 68527032, compound

Product 1

HCID 68524472HCID 68524472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1-{4-[5-(3,4-dichlorobenzenesulfonylamino)pyridin-2-yloxy]-3-methylphenyl}piperidine-4-yl)acetic acid (1.70 g, 3.1 mmol) and 1-benzylpiperazine (0.71 g, 4.0 mmol) in DMF (40 mL) were added triethylamine (1.08 mL, 7.8 mmol) and diethyl cyanophosphonate (0.76 g, 4.3 mmol) under ice cooling, and the resulting solution was stirred for 1 hour under ice cooling. To this reaction solution was added a saturated sodium bicarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1), after which the resulting product was recrystallized from ethanol, to thereby yield 1.61 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1)
  6. customafter which the resulting product was recrystallized from ethanol

Sources & evidence

ORD record
ord-718cdd17d448477fbf8fdb3caf1c28ef
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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