Acetamidine monohydrochloride → HCID 136388714, compound

HRID 389305Notes

Reaction equation

HRID 389305 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=O)[CH2:7][N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][C:15]2[CH:23]=[C:22]([CH3:24])[C:21]([O:25][CH3:26])=[C:20]3[C:16]=2[CH2:17][CH2:18][CH2:19]3)[C:10]([CH3:27])=[N:9]1)C.Cl.[C:31]([NH2:34])(=[NH:33])[CH3:32].[O-]CC.[Na+]>C(O)C>[CH3:26][O:25][C:21]1[C:22]([CH3:24])=[CH:23][C:15]([CH2:14][C:11]2[C:10]([CH3:27])=[N:9][N:8]([CH2:7][C:6]3[N:33]=[C:31]([CH3:32])[NH:34][C:4](=[O:3])[CH:5]=3)[C:12]=2[CH3:13])=[C:16]2[C:20]=1[CH2:19][CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 66812423HCID 66812423, compound

Product 1

HCID 136388714HCID 136388714, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
72.5 °C

Procedure

To the solution of 4-[4-(7-Methoxy-6-methyl-indan-4-ylmethyl)-3,5-dimethyl-pyrazol-1-yl]-3-oxo-butyric acid ethyl ester (1.0 gm, 0.0025 mole) in Ethanol (60 ml), Acetamidine hydrochloride (0.71 gm, 0.0075 mole) was added. Further to this, Sodium ethoxide (0.51 gm, 0.0075 mole) was added at 5-10° C. and then stirred at 70-75° C. for 2 hours. The Ethanol was distilled under vacuum and residue was partitioned between Ethyl acetate (100 ml) and water (100 ml). Further aqueous layer was extracted with Ethyl acetate (2×100 ml). The combined volume of Ethyl acetate layer was reduced to 20 ml and then filtered to give 800 mg of desired product.

Workup

  1. distillationThe Ethanol was distilled under vacuum and residue
  2. customwas partitioned between Ethyl acetate (100 ml) and water (100 ml)
  3. extractionFurther aqueous layer was extracted with Ethyl acetate (2×100 ml)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c40e0069ed484298979565de8adc948d
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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