3,4,5-Trimethoxyaniline → [7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine

HRID 1261932Notes

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][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:6]2[N:5]=1)=O.C(N(CC)C(C)C)(C)C.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[NH2:37]>COCCO>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:37][C:36]4[CH:38]=[C:39]([O:43][CH3:44])[C:40]([O:41][CH3:42])=[C:34]([O:33][CH3:32])[CH:35]=4)=[N:5]3)=[CH:10][CH:11]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 180 °C

Procedure

2-Methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (125 mg, 0.000373 mol), N,N-Diisopropylethylamine (0.0974 mL, 0.000559 mol) and 3,4,5-Trimethoxyaniline (81.9 mg, 0.000447 mol) were dissolved in 2-Methoxyethanol (2.2 mL) and the reaction was heated at 180° C. under 300 W microwave conditions 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 24.45 mg of [7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine as a lyophilated powder. (M+H)=455.14. 1H NMR (400 MHz, CDCl3) δ 9.11 (m, 1H), 8.73 (s, 1H), 8.34 (d, 2H, J=8.59 Hz), 8.05 (d, 2H, J=8.34 Hz), 7.23 (m, 1H), 7.18 (d, 1H, J=5.05 Hz), 6.87 (s, 2H), 3.86 (s, 3H), 3.77 (s, 6H), 3.25 (s, 3H).

Workup

customconsumption of starting material
customthe product was isolated
custompurified by Gilson prep HPLC

Sources & evidence

ORD record: ord-1b470c8dccb44924836acdeff8cfea82
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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