[5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine → [7-(4-Methanesulfonyl-phenyl)-5-vinyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1261902Notes

Reaction equation

HRID 1261902 reaction equation
Br[C:2]1C=C(C2C=CC=CC=2OC)N2[C:10]=1C=NC(NC1C=CC(N3CCN(C)CC3)=CC=1)=N2.Br[C:34]1[CH:35]=[C:36]([C:57]2[CH:62]=[CH:61][C:60]([S:63]([CH3:66])(=[O:65])=[O:64])=[CH:59][CH:58]=2)[N:37]2[C:42]=1[CH:41]=[N:40][C:39]([NH:43][C:44]1[CH:49]=[CH:48][C:47]([N:50]3[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]3)=[CH:46][CH:45]=1)=[N:38]2>>[CH3:66][S:63]([C:60]1[CH:59]=[CH:58][C:57]([C:36]2[N:37]3[C:42]([CH:41]=[N:40][C:39]([NH:43][C:44]4[CH:45]=[CH:46][C:47]([N:50]5[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]5)=[CH:48][CH:49]=4)=[N:38]3)=[C:34]([CH:2]=[CH2:10])[CH:35]=2)=[CH:62][CH:61]=1)(=[O:64])=[O:65]

Participants

3

Reactant 2

HCID 66710869[5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amineHCID 66711068[5-Bromo-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Product 1

HCID 66711218[7-(4-Methanesulfonyl-phenyl)-5-vinyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amineYield 63%

Procedure

The tited compound was prepare in an analogous fashion to Example 103 replacing [5-Bromo-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine with [5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine to give [7-(4-Methanesulfonyl-phenyl)-5-vinyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (45 mg, 63%). LCMS (E/I+) 489.21 (M+H). NMR 1H (DSMO-d6)-9.23 (s, 1H), 8.99 (s, 1H), 8.48 (d, 2H, J=8.44 Hz), 8.07 (d, 2H, J=8.56 Hz), 7.66 (d, 2H, J=9.01 Hz), 7.00-7.18 (m, 2H), 7.00 (d, 2H, J=8.88 Hz), 5.82 (d, 1H, J=16.95 Hz), 5.21 (d, 1H, J=12.21 Hz), 3.80 (s, 3H), 3.02 (t, 4H, J=4.60 Hz), 2.44 (t, 4H, J=4.72 Hz), 2.21 (s, 3H).

Sources & evidence

ORD record
ord-983eab7b21b945cb867448f0a49d3753
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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