Acetamidine monohydrochloride → HCID 178433956, compound

HRID 331960Notes

Reaction equation

HRID 331960 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([NH:21][NH2:22])=O)=[CH:17][N:16]=1.Cl.[C:26](N)(=[NH:28])[CH3:27]>CN(C=O)C.C(OC(=O)C)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]2[NH:28][C:26]([CH3:27])=[N:22][N:21]=2)=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 67170Acetamidine monohydrochloride2×HCID 498009746-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid hydrazide

Product 1

HCID 178433956HCID 178433956, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid hydrazide (300 mg, 0.6 mmol) and acetamidine hydrochloride (87 mg, 0.9 mmol) in DMF (6 mL) was heated at 120° C. for 2 h. A second portion of acetamidine hydrochloride (174 mg, 1.8 mmol) was added. After 8 h the mixture was cooled to room temperature and diluted with ethylacetate (40 mL). The mixture was filtered and the filtrates collected and washed with water (3×10 mL) and brine (10 mL) then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (SiO2, 0-5% dichloromethane:methanol=100:0 to 95:5) followed by purification by HPLC (acetonitrile:water=2:8) gave the title compound (42 mg, 20%) as a white solid. MS: m/e=348.2 [M+H]+.

Workup

  1. temperatureAfter 8 h the mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. customthe filtrates collected
  4. washwashed with water (3×10 mL) and brine (10 mL)
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (SiO2, 0-5% dichloromethane:methanol=100:0 to 95:5)
  9. customfollowed by purification by HPLC (acetonitrile:water=2:8)

Sources & evidence

ORD record
ord-00a4d6c351714f45bf5c6a33f55ea5d0
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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