Diisopropylethylamine → HCID 178462948, compound

HRID 1582991Notes

Reaction equation

HRID 1582991 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5](=[O:24])[N:6]([CH2:22][CH3:23])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)=[CH:11][CH:10]=[C:9]([CH3:21])[N:8]=2.Cl.[C:26](N1C=CC=N1)(=[NH:28])[NH2:27].C(N(C(C)C)CC)(C)C>O1CCOCC1>[OH2:24].[ClH:20].[Cl:20][C:16]1[CH:15]=[C:14]([C:13]2[C:12]3[C:7](=[N:8][C:9]([CH3:21])=[CH:10][CH:11]=3)[N:6]([CH2:22][CH3:23])[C:5](=[O:24])[C:4]=2[CH2:3][CH2:2][NH:1][C:26]([NH2:28])=[NH:27])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 12991183HCID 12991183, compound

Product 1

HCID 178462948HCID 178462948, compoundYield 172.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 15 ml 1,4-dioxane solution containing 314 mg of 3-(2-aminoethyl)-4-(3-chlorophenyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one were added 404 mg of 1-amidinopyrazole monohydrochloride and 0.48 ml of diisopropylethylamine, followed by stirring for 122 hours. The reaction solution was evaporated, the resulting solid was removed by filtration, and the solid was further washed with chloroform. The combine filtrate and washings were concentrated and the residue was purified by a silica gel column chromatography (chloroform-methanol-aqueous ammonia). The resulting oily substance was dissolved in 5 ml of ethanol, and 0.5 ml of 4M hydrogen chloride-ethyl acetate and acetonitrile were added thereto successively. The solvent was evaporated to obtain 347 mg of 4-(3-chlorophenyl)-1-ethyl-3-(2-guanidinoethyl)-7-methyl-1,8-naphthyridin-2(1H)-one monohydrochloride monohydrate as a colorless solid.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting solid was removed by filtration
  3. washthe solid was further washed with chloroform
  4. concentrationThe combine filtrate and washings were concentrated
  5. customthe residue was purified by a silica gel column chromatography (chloroform-methanol-aqueous ammonia)
  6. dissolutionThe resulting oily substance was dissolved in 5 ml of ethanol
  7. addition0.5 ml of 4M hydrogen chloride-ethyl acetate and acetonitrile were added
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-74e02a9fb3b04254b86fcd51cde21eca
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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