1-(4-Nitrophenyl)piperazine → HCID 66712003, compound

HRID 1261959Notes

Reaction equation

HRID 1261959 reaction equation
[N+]([C:4]1C=C(N2CCNCC2)C=CC=1)([O-])=O.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)([O-])=O.CS(C1N=CC2=CC=C([C:43]3C=CC=[CH:45][C:44]=3[O:49]C)N2N=1)=O.[Cl:51][C:52]1[CH:53]=[C:54]([C:58]2[N:66]3[C:61]([CH:62]=[N:63][C:64](S(C)=O)=[N:65]3)=[CH:60][CH:59]=2)[CH:55]=[CH:56][CH:57]=1>>[Cl:51][C:52]1[CH:53]=[C:54]([C:58]2[N:66]3[C:61]([CH:62]=[N:63][C:64]([NH:16][C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH2:43][C:44]([CH3:4])([OH:49])[CH3:45])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)=[N:65]3)=[CH:60][CH:59]=2)[CH:55]=[CH:56][CH:57]=1

Participants

5

Reactant 4

HCID 804471-(4-Nitrophenyl)piperazineHCID 27602161-(3-Nitrophenyl)piperazineHCID 66710773HCID 66710773, compoundHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66712003HCID 66712003, compound

Procedure

The compound was prepared in an analogous fashion to Example 85 replacing 1-(3-Nitro-phenyl)-piperazine with 1-(4-Nitro-phenyl)-piperazine and 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine with 7-(3-Chloro-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine to afford 22.28 mg of 1-(4-{4-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperazin-1-yl)-2-methyl-propan-2-ol as a lyophilized powder. (M+H)=477.8. 1H NMR (400 MHz, DMSO, d6) δ 9.39 (s, 1H), 8.99 (s, 1H), 8.49 (s, 1H), 8.03 (d, 1H, J=7.93 Hz), 7.67 (d, 2H, J=8.92 Hz), 7.54 (t, 1H, J=7.97 Hz), 7.44 (m, 1H), 7.26 (d, 1H, J=4.76 Hz), 7.01 (d, 2H, J=8.96 Hz), 6.95 (d, 1H, J=4.76 Hz), 3.63 (m, 4H), 3.25 (m, 6H), 1.31 (s, 6H).

Sources & evidence

ORD record
ord-edd018a24e0348d3aed64c5897f2fea9
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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