Acetamidine monohydrochloride → HCID 136388714, compound

HRID 1099357Notes

Reaction equation

HRID 1099357 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-127112c453fe4a09ad0179444cdba0e2
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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