Sodium Carbonate → 8-[(4-Methoxybenzyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44621Notes

Reaction equation

HRID 44621 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH2:18])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.CO.O>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:1][C:2]2[N:11]=[CH:10][C:9]3[CH2:8][CH2:7][C:6]4[C:12]([C:16]([NH2:18])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=4[C:4]=3[N:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312444-MethoxybenzaldehydeHCID 5003444Sodium cyanoborohydride2×HCID 45140384HCID 45140384, compound

Product 1

HCID 451418008-[(4-Methoxybenzyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 86607755Acetic acid methanol waterSolvent

Procedure

To a solution of 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (244 mg, 1.0 mmol) in a mixture of glacial acetic acid/methanol/water (1:1:1) (30 mL) in a round-bottom flask were added p-methoxybenzaldehyde (0.44 mL, 450 mg, 3.0 mmol) and then 85% sodium cyanoborohydride (210 mg, 2.0 mmol). The solution was stirred at room temperature for 7 hours. At that time further amount of aldehyde (0.44 mL) and sodium cyanoborohydride (210 mg) were added and stirring was continued overnight. The reaction mixture was poured into ice-water (200 mL), the pH was adjusted to 10 by addition of saturated sodium carbonate and the solution extracted with ethyl acetate (4×20 mL). The collected organic extracts were washed with brine until neutral, with water and dried over Na2SO4.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionthe solution extracted with ethyl acetate (4×20 mL)
  4. washThe collected organic extracts were washed with brine until neutral, with water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-50c62c8bab3949bab18305ee36a8ca1e
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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