P-Anisidine → HCID 66711042, compound

HRID 1261929Notes

Reaction equation

HRID 1261929 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:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>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:30][C:27]4[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 66710941HCID 66710941, compound

Product 1

HCID 66711042HCID 66711042, compoundYield 14%

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 4-Methoxybenzenamine (57.4 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 12.41 mg of [7-(5-Chloro-2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-methoxy-phenyl)-amine as a lyophilized powder. (M+H)=381.11. 1H NMR (400 MHz, DMSO, d6) δ 9.29 (s, 1H), 8.95 (s, 1H), 8.05 (m, 1H), 7.63 (d, 2H, J=9.09 Hz), 7.46 (m, 1H), 7.23 (d, 1H, J=8.84 Hz), 7.03 (d, 1H, J=4.55 Hz), 6.90 (d, 1H, J=4.55 Hz), 6.85 (m, 2H), 3.82 (s, 3H), 3.70 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-845f1672a19d4645bf50eb56a24b6b71
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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