Triethylamine → 8-(Cyclopentylamino)-N-hydroxy-N,1-dimethyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44608

Reaction equation

HRID 44608 reaction equation
[CH:1]1([NH:6][C:7]2[N:16]=[CH:15][C:14]3[CH2:13][CH2:12][C:11]4[C:17]([C:21]([O-])=[O:22])=[N:18][N:19]([CH3:20])[C:10]=4[C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[K+].C(Cl)(=O)C(Cl)=O.Cl.[CH3:32][NH:33][OH:34].C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH:1]1([NH:6][C:7]2[N:16]=[CH:15][C:14]3[CH2:13][CH2:12][C:11]4[C:17]([C:21]([N:33]([OH:34])[CH3:32])=[O:22])=[N:18][N:19]([CH3:20])[C:10]=4[C:9]=3[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 45140959Potassium 8-(cyclopentylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Product 1

HCID 451394278-(Cyclopentylamino)-N-hydroxy-N,1-dimethyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 199.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 400 mg (1.14 mmol) of potassium 8-(cyclopentylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in 80 mL of dichloromethane and a few drops of dimethylformamide 0.11 mL (0.13 mmol) of oxalyl chloride were added at 0° C. The mixture was stirred at room temperature for 6 hours and then evaporated, redissolved in anhydrous dichloromethane and dropped into a solution of 344 mg (2.28 mmol) of N-methylhydroxylamine hydrochloride and 0.33 mL of triethylamine in 20 mL of the same solvent, cooled to 0° C. After 4 hours the mixture was washed with a saturated solution of sodium hydrogenocarbonate, dried over sodium sulfate and evaporated to dryness. The residue was triturated with diethylether and filtered to give 780 mg (60% yield) of the title compound.

Workup

  1. additionwere added at 0° C
  2. customevaporated
  3. dissolutionredissolved in anhydrous dichloromethane
  4. temperaturecooled to 0° C
  5. washAfter 4 hours the mixture was washed with a saturated solution of sodium hydrogenocarbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was triturated with diethylether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-0d1bedce630f49159deaf5a937a38ece
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Linked notes

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