Sodium Hydroxide → HCID 11718226, compound

HRID 1894810Notes

Reaction equation

HRID 1894810 reaction equation
[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[Na+].C(NC(=O)N(C1N=C(C2C=CC(CCC(OCC)=O)=CC=2)C=CC=1)C)CCCCCC.O1CCCC1.CO>CO.[Pd].C(O)(=O)C.O>[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 66590273HCID 66590273, compoundHCID 66591184HCID 66591184, compound

Product 1

HCID 11718226HCID 11718226, compoundYield 69.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

170 mg (0.4 mmol) of ethyl 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate are dissolved in 5 ml of methanol. 50 mg of 10% palladium-on-charcoal are added. The reaction mixture is stirred for 3 hours at room temperature under a hydrogen atmosphere. The catalyst is filtered off and the solvents are then evaporated off and the oil obtained is used directly in the following reaction. 170 mg of sodium hydroxide are added to the solution of ethyl 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate in 5 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for two hours at room temperature. The reaction is stopped by adding 20 mL of water and 3 mL of acetic acid and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (7/3 to 1/1 heptane/EtOAc). 110 mg of 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoic acid are obtained. Yield=69% over two steps. m.p.=108° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvents are then evaporated off
  3. customthe oil obtained
  4. customis used directly in the following reaction
  5. stirringThe reaction mixture is stirred for two hours at room temperature
  6. extractionis then extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. customThe solvents are evaporated off
  9. customthe residue is then chromatographed on silica gel (7/3 to 1/1 heptane/EtOAc)

Sources & evidence

ORD record
ord-b622b9337996464f9b7a955905407802
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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