1,3-Benzodioxol-5-amine → HCID 66711222, compound

HRID 1261927Notes

Reaction equation

HRID 1261927 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=2[O:23][CH2:22]1>COCCO>[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([NH:30][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[O:19][CH3:20])[N:6]4[N:5]=3)=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

4

Reactant 2

HCID 843101,3-Benzodioxol-5-amineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711222HCID 66711222, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
180 °C

Procedure

2-Methane sulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (67.0 mg, 0.000233 mol) and 1,3-Benzodioxol-5-ylamine (63.9 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 2.65 mg 1,3-Benzodioxol-5-yl-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine as a lyophilated powder. (M+H)=361.20. 1H NMR (400 MHz, DMSO, d6) δ 9.29 (s, 1H), 8.93 (s, 1H), 7.75 (d, 1H, J=7.07 Hz), 7.51 (s, 1H), 7.46 (m, 1H), 7.20 (m, 1H), 7.10 (m, 2H), 7.05 (s, 2H), 6.76 (d, 1H, J=8.34 Hz), 5.94 (s, 2H), 3.79 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-bf60e833282c402ca0e921d0206fbd23
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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