Hydrochloric Acid → N-methyl-1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-amine

HRID 2389248Notes

Reaction equation

HRID 2389248 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([C:26]3[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=3)=[N:18][N:17]=2)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.Cl.C(OCC)C>ClCCl>[CH3:1][NH:2][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([C:26]3[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=3)=[N:18][N:17]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59627389tert-butyl methyl(1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-yl)carbamate

Product 1

HCID 59627388N-methyl-1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-amineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve tert-butyl methyl(1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-yl)carbamate (7.77 g, 18.39 mmol) in dichloromethane (100 mL). Add an excess of 1 M hydrogen chloride in diethyl ether (20 mL, 80 mmol) to the solution and stir at ambient temperature for 2 h. Concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (dichloromethane:2 M NH3 in MeOH=10:1) to provide the title compound as a yellow foam (5.83 g, 98%). ES/MS m/z 323.2 (M+1).

Workup

  1. concentrationConcentrate under reduced pressure
  2. customPurify the resulting residue by flash silica gel chromatography (dichloromethane:2 M NH3 in MeOH=10:1)

Sources & evidence

ORD record
ord-b5d2c9ccf1d447db9962d5aa7426bb58
Source dataset
uspto-grants-2012_09
Patent number
US08273742B2

Reaction notes

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