Cyclohexylamine → HCID 11416146, compound

HRID 875090Notes

Reaction equation

HRID 875090 reaction equation
[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11](S(C)(=O)=O)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:19]([NH2:21])=[O:20])=[N:3]1.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CS(C)=O>[CH:22]1([NH:28][C:11]2[N:10]=[CH:9][C:8]3[CH:7]=[CH:6][C:5]4[C:4]([C:19]([NH2:21])=[O:20])=[N:3][N:2]([CH3:1])[C:14]=4[C:13]=3[N:12]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[CH:22]1([NH:28][C:11]2[N:10]=[CH:9][C:8]3[CH2:7][CH2:6][C:5]4[C:4]([C:19]([NH2:21])=[O:20])=[N:3][N:2]([CH3:1])[C:14]=4[C:13]=3[N:12]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 116524591-methyl-8-(methylsulfonyl)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 2

HCID 11416146HCID 11416146, compoundHCID 116527368-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.5 g of 1-methyl-8-(methylsulfonyl)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide were dissolved in 100 mL of dry dimethylsulfoxide and 1.15 mL of cyclohexylamine were added. After 16 hours at 80° C. under nitrogen the solvent was evaporated at reduced pressure. The residue was then redissolved with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and evaporated to dryness. By chromatography on a silica gel column (eluant dichloromethane/acetone 9/1) 300 mg of 8-(cyclohexylamino)-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide and 200 mg of 8-(cyclohexylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide and were obtained (30% yield overall).

Workup

  1. customAfter 16 hours at 80° C. under nitrogen the solvent was evaporated at reduced pressure
  2. dissolutionThe residue was then redissolved with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-84acbabbfe7c4256a1aab7eb81048580
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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