3,4-Dimethoxyaniline → HCID 66711466, compound

HRID 1261928Notes

Reaction equation

HRID 1261928 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14](S(C)=O)=[N:15]3)=[CH:10][CH:9]=2)[CH:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[NH2:27]>COCCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:27][C:26]4[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:24]([O:23][CH3:22])[CH:25]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 227703,4-DimethoxyanilineHCID 66710941HCID 66710941, compound

Product 1

HCID 66711466HCID 66711466, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
180 °C

Procedure

[7-(5-Chloro-2-methoxy-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (75.0 mg, 0.000233 mol) and 3,4-dimethoxyaniline (71.4 mg, 0.000466 mol) were dissolved in 2-Methoxyethanol (1.64 mL) and the reaction was heated at 180° C. until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 32.66 mg of [7-(5-Chloro-2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3,4-dimethoxy-phenyl)-amine as a lyophilized powder. (M+H)=411.12. 1H NMR (400 MHz, DMSO, d6) δ 9.24 (s, 1H), 8.95 (s, 1H), 7.93 (s, 1H), 7.48 (m, 1H), 7.31 (m, 2H), 6.97 (d, 1H, J=4.80 Hz), 6.82 (d, 1H, J=8.34 Hz), 6.26 (m, 1H), 6.05 (dd, 1H, J=2.52, 6.07 Hz), 3.79 (s, 3H), 3.69 (s, 3H), 3.65 (s, 3H).

Workup

  1. customconsumption of starting material
  2. customthe product was isolated
  3. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-532c56b57bcb4d1e9786434c76bb6550
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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