1-Methoxy-2-propanol → 1-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-1H-imidazo[4,5-c]pyridine

HRID 1261983Notes

Reaction equation

HRID 1261983 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.C(N(CC)C(C)C)(C)C.[NH:30]1[C:38]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[N:32]=[CH:31]1.COCC(O)C>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([N:30]3[C:38]4[CH:37]=[CH:36][N:35]=[CH:34][C:33]=4[N:32]=[CH:31]3)=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 178419860HCID 178419860, compound

Product 1

HCID 667111881-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-1H-imidazo[4,5-c]pyridineYield 29.4%

Procedure

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (125.0 mg, 0.0004350 mol), N,N-Diisopropylethylamine (0.114 mL, 0.000652 mol) and 1H-Imidazo[4,5-c]pyridine (0.104 g, 0.000870 mol) were dissolved in 1-Methoxy-2-propanol (1.2 mL, 0.013 mol) and the reaction was irradiated at 300 watts, 180° C. for 40 minutes or 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 43.80 mg of 1-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-1H-imidazo[4,5-c]pyridine (mixture of regioisomers) as a lyophilized powder. (M+H)=343.7. 1H NMR (400 MHz, DMSO, d6) δ 9.35 (s, 1H), 9.15 (s, 1H), 8.47 (d, 1H, J=5.52 Hz), 8.09 (d, 1H, J=5.45 Hz), 7.81 (m, 2H), 7.57 (m, 1H), 7.32 (m, 3H), 7.23 (m, 1H), 3.82 (s, 3H).

Workup

  1. customthe reaction was irradiated at 300 watts, 180° C. for 40 minutes or until HPLC
  2. customconsumption of starting material
  3. customthe product was isolated
  4. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-b362024daef0424d9fd1135038a2b582
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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