3,4,5-Trimethoxyaniline → HCID 66710850, compound

HRID 1261924Notes

Reaction equation

HRID 1261924 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]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[NH2:27]>CN1CCCC1=O>[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]=[C:29]([O:33][CH3:34])[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 322853,4,5-TrimethoxyanilineHCID 66710941HCID 66710941, compound

Product 1

HCID 66710850HCID 66710850, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °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 3,4,5-Trimethoxyaniline (51 mg, 0.00028 mol) were dissolved in N-Methylpyrrolidinone (5.00 mL) and the reaction was heated at 140° 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 29.22 mg of [7-(5-Chloro-2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine as a lyophilated powder. (M+H)=441.09. 1H NMR (400 MHz, DMSO, d6) δ 9.29 (s, 1H), 8.97 (s, 1H), 7.73 (s, 1H), 7.45 (m, 1H), 7.22 (d, 1H, J=8.84 Hz), 7.02 (s, 2H), 6.92 (m, 2H), 3.76 (s, 3H), 3.57 (s, 3H), 3.49 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-a2517af17c6e473bad0d39d70dc5fc62
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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