Phenyl triflimide → 5-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-nicotinamide

HRID 1262106Notes

Reaction equation

HRID 1262106 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](O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.[NH2:40][C:41]1[CH:42]=[N:43][CH:44]=[C:45]([CH:49]=1)[C:46]([NH2:48])=[O:47]>>[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:40][C:41]4[CH:42]=[N:43][CH:44]=[C:45]([CH:49]=4)[C:46]([NH2:48])=[O:47])=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 142176Phenyl triflimideHCID 1737473-Pyridinecarboxamide, 5-amino-HCID 178488500HCID 178488500, compound

Product 1

HCID 667108315-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-nicotinamideYield 40%

Procedure

The titled compound was prepared in analogous fashion as Example 522 using 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol, N-phenylbis(trifluoromethanesulphonimide) and 5-amino-nicotinamide to give 5-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-nicotinamide as a light brown solid (23.9 mg, 40% yield). M.p.=>250° C. LCMS (E/I+) 361 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 9.85 (s, 1H), 9.05 (s, 1H), 8.92 (s, 1H), 8.83 (s, 1H), 8.60 (m, 3H), 8.09 (s, 1H), 7.62 (s, 1H), 7.25 (d, 1H, J=4.7 Hz), 7.02 (m, 2H), 3.92 (s, 3H).

Sources & evidence

ORD record
ord-413250d6acae4cc7a53fd991ee1fd6cf
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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