3-Methoxyaniline → HCID 66711100, compound

HRID 1261925Notes

Reaction equation

HRID 1261925 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][CH:30]=1)[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]=[CH:29][CH:30]=[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 108243-MethoxyanilineHCID 66710941HCID 66710941, compound

Product 1

HCID 66711100HCID 66711100, compoundYield 9.1%

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 [B] 3-methoxyaniline (57.4 mg, 0.000466 mol) were dissolved in N-Methylpyrrolidinone (2.0 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 8.08 mg of [7-(5-Chloro-2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-methoxy-phenyl)-amine as a lyophilated powder. (M+H)=381.09. 1H NMR (400 MHz, DMSO, d6) δ 9.44 (s, 1H), 8.98 (s, 1H), 7.89 (s, 1H), 7.49 (m, 1H), 7.37 (m, 1H), 7.24 (m, 3H), 7.01 (d, 1H, J=4.55 Hz), 6.94 (d, 1H, J=4.55 Hz), 6.50 (d, 1H, J=8.34 Hz), 3.80 (s, 3H), 3.60 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-764642ed7d934d4da76c1c431f1be70a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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