1-(4-methoxyphenyl)-N-methylmethanamine → N-(4-methoxybenzyl)-N,7-dimethyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazin-4-amine

HRID 1907200Notes

Reaction equation

HRID 1907200 reaction equation
[N:1]1([C:5]2[C:10]3=[C:11]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[N:12]=[C:13]([CH3:14])[N:9]3[N:8]=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27]C(CNC)=[CH:25][CH:24]=1.Cl.N1CCC1>>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:3]([CH2:4][N:1]([CH3:2])[C:5]2[C:10]3=[C:11]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[N:12]=[C:13]([CH3:14])[N:9]3[N:8]=[CH:7][N:6]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 4854071-(4-methoxyphenyl)-N-methylmethanamineHCID 12308726Azetidine hydrochlorideHCID 681820894-(Azetidin-1-yl)-7-methyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazine

Product 1

HCID 68182074N-(4-methoxybenzyl)-N,7-dimethyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazin-4-amine

Procedure

The product was synthesized in a manner similar to that described for the preparation of 4-(azetidin-1-yl)-7-methyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazine in Example 2, except that 1-(4-methoxyphenyl)-N-methylmethanamine was utilized in place of azetidine hydrochloride, and the workup was modified somewhat: after the slurry was extracted with dichloromethane, the combined organic layers were washed with 1 N aqueous sodium hydroxide solution, washed with saturated aqueous sodium chloride solution, and dried over sodium sulfate. After filtration, the filtrate was concentrated in vacuo and passed through a short column of silica gel (Eluant: 5% methanol in ethyl acetate). The eluant was concentrated under reduced pressure, and the resulting solid was washed with tert-butyl methyl ether followed by diethyl ether, to provide C6. Yield: 36.0 g, 99.1 mmol, 76%. LCMS m/z 364.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.67 (s, 3H), 2.84 (s, 3H), 3.77 (s, 3H), 3.88 (s, 3H), 4.66 (s, 2H), 6.82 (br d, J=8.7 Hz, 2H), 7.07 (br d, J=8.6 Hz, 2H), 7.58 (s, 1H), 7.62 (s, 1H), 7.89 (s, 1H).

Workup

  1. customThe product was synthesized in a manner similar to
  2. extractionafter the slurry was extracted with dichloromethane
  3. washthe combined organic layers were washed with 1 N aqueous sodium hydroxide solution
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. concentrationThe eluant was concentrated under reduced pressure
  9. washthe resulting solid was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-816804b7f3f04d52a091b46895dab481
Source dataset
uspto-grants-2013_12
Patent number
US08598155B2

Reaction notes

Loading…