4-Amino-1-methylpiperidine → 1-methyl-8-[(1-methylpiperidin-4-yl)amino]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44611

Reaction equation

HRID 44611 reaction equation
I[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][N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1>>[CH3:15][N:14]1[C:5]2[C:4]3[N:3]=[C:2]([NH:26][CH:23]4[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]4)[N:11]=[CH:10][C:9]=3[CH2:8][CH2:7][C:6]=2[C:12]([C:16]([NH2:18])=[O:17])=[N:13]1

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 442356528-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 451397981-methyl-8-[(1-methylpiperidin-4-yl)amino]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 50%

Procedure

8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (0.10 g, 0.28 mmol) and 1-methylpiperidin-4-amine (0.19 g, 1.7 mmol) were heated at 80° C. under nitrogen for 3 hours. The mixture was concentrated under reduced pressure and the residue was purified by chromatography on a silica gel column (eluant: dichloromethane/ethanol/ammonium hydroxide 90/10/1) to give 0.047 mg of 1-methyl-8-[(1-methylpiperidin-4-yl)amino]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (50% yield).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on a silica gel column (eluant: dichloromethane/ethanol/ammonium hydroxide 90/10/1)

Sources & evidence

ORD record
ord-5e763ad141a6413ca9dd83da1b890fdf
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Linked notes

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