Cyclohexylamine → HCID 11416146, compound

HRID 1455092Notes

Reaction equation

HRID 1455092 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-890e3e2c0b844a45b3bb2cd3a5a1aa87
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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