Sodium Bicarbonate → HCID 59233146, compound

HRID 1925153Notes

Reaction equation

HRID 1925153 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[CH2:30][NH2:31].[C:32]([O-])(O)=O.[Na+]>CC(O)C>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[CH2:30][NH:31][C:16]1[N:15]=[N:14][C:13]([CH:11]([C:8]2[N:6]3[CH:7]=[C:2]([CH3:32])[CH:3]=[CH:4][C:5]3=[N:10][N:9]=2)[CH3:12])=[CH:18][CH:17]=1.[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[N:14]=[N:15][C:16]([NH:31][CH2:30][C:23]4[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=4[O:21][CH3:20])=[CH:17][CH:18]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 59233097HCID 59233097, compound

Product 2

HCID 59233146HCID 59233146, compoundYield 166.5%HCID 67072739HCID 67072739, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-bromo-3-(1-(6-chloropyridazin-3-yl)ethyl)-[1,2,4]triazolo[4,3-a]pyridine (650 mg, 1.920 mmol), (2,4-dimethoxyphenyl)methanamine (0.577 mL, 3.84 mmol), and NaHCO3 (645 mg, 7.68 mmol) in IPA (10.0 mL) was heated in a microwave on high absorbance for 18 hrs at 140° C. The reaction was cooled to ambient temperature, stripped to dryness via rotary evaporation, and reconstituted in EtOAc (25 mL). The insolubles were filtered off and the filtrate was reduced to dryness. The resulting residue was purified via MPLC (DCM:MeOH, 98:2) to provide the title compound, 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine 48E (750 mg, 1.598 mmol, 83% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.77 (d, J=7.07 Hz, 3 H) 3.72 (s, 3 H) 4.37 (d, J=5.81 Hz, 2 H) 4.95 (d, J=7.07 Hz, 1H) 6.44 (dd, J=8.34, 2.53 Hz, 1 H) 6.54 (d, J=2.27 Hz, 1 H) 6.85 (d, J=9.35 Hz, 1H) 7.03 (s, 1 H) 7.12 (d, J=8.34 Hz, 1 H) 7.29 (d, J=9.35 Hz, 1 H) 7.45 (dd, J=9.73, 1.64 Hz, 1 H) 7.69-7.79 (m, 1 H) 8.59 (s, 1 H). ESI-MS:m/z 469.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customstripped to dryness via rotary evaporation
  3. filtrationThe insolubles were filtered off
  4. customThe resulting residue was purified via MPLC (DCM:MeOH, 98:2)

Sources & evidence

ORD record
ord-4b9098833a1f41e58009516c1c079c2a
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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