4-(1,2,3-Thiadiazol-4-yl)aniline → [7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-[1,2,3]thiadiazol-4-yl-phenyl)-amine

HRID 1262142Notes

Reaction equation

HRID 1262142 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[S:26]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[N:28]=[N:27]1>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:37][C:34]4[CH:33]=[CH:32][C:31]([C:29]5[N:28]=[N:27][S:26][CH:30]=5)=[CH:36][CH:35]=4)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 27391704-(1,2,3-Thiadiazol-4-yl)anilineHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66711571[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-[1,2,3]thiadiazol-4-yl-phenyl)-amineYield 24%

Procedure

Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (0.138 g, 0.369 mmol and 4-[1,2,3]Thiadiazol-4-yl-phenylamine (0.0817 g, 0.461 mmol) were reacted in an analogous manner to Example 908D at 50° overnight. The reaction mixture was filtered and the resulting solid was washed with acetone to give the title compound as a pale yellow solid (36 mg, 24%). HPLC rt=3.347, purity=99%. LCMS=401.9 (M+H). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.81 (s, 1H), 9.52 (s, 1H), 9.04 (s, 1H), 8.93 (d, J=2.0 Hz, 1H), 8.54 (dd, J=8.7 Hz, 2.3 Hz, 1H), 8.08 (d, J=7.9 Hz, 2H), 7.91 (d, J=8.6 Hz, 2H), 7.21 (d, J=4.4 Hz, 1H), 7.08 (d, J=8.7 Hz, 1H), 7.00 (d, J=4.3 Hz, 1H), 3.96 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resulting solid was washed with acetone

Sources & evidence

ORD record
ord-be0385b0993c42199a5841f7ee61cdc4
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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