1-(4-Nitrophenyl)piperazine → HCID 66711332, compound

HRID 1261954Notes

Reaction equation

HRID 1261954 reaction equation
[N+](C1C=CC(N2CCNCC2)=CC=1)([O-])=O.[N+:16]([C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1)([O-])=O.CS(C1N=CC2=CC=C([C:43]3C=CC=[CH:45][C:44]=3[O:49]C)N2N=1)=O.CS([C:54]1[N:59]=[CH:58][C:57]2=[CH:60][CH:61]=[C:62]([C:63]3[CH:68]=[CH:67][C:66]([S:69]([CH3:72])(=[O:71])=[O:70])=[CH:65][CH:64]=3)[N:56]2[N:55]=1)=O>>[CH3:72][S:69]([C:66]1[CH:67]=[CH:68][C:63]([C:62]2[N:56]3[C:57]([CH:58]=[N:59][C:54]([NH:16][C:19]4[CH:20]=[C:21]([N:25]5[CH2:30][CH2:29][N:28]([CH2:43][C@H:44]([OH:49])[CH3:45])[CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)=[N:55]3)=[CH:60][CH:61]=2)=[CH:64][CH:65]=1)(=[O:71])=[O:70]

Participants

5

Reactant 4

HCID 804471-(4-Nitrophenyl)piperazineHCID 27602161-(3-Nitrophenyl)piperazineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 667110462-(Methylsulfinyl)-7-(4-(methylsulfonyl)phenyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711332HCID 66711332, compound

Procedure

The compound was prepared in an analogous fashion to Example 73 replacing 1-(4-Nitro-phenyl)-piperazine with 1-(3-Nitro-phenyl)-piperazine and 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine with 2-Methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine to afford 44.32 mg of (R)-1-(4-{3-[7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperazin-1-yl)-propan-2-ol as a lyophilized powder. (M+H)=507.10. 1H NMR (400 MHz, DMSO, d6) δ 9.49 (s, 2H), 9.08 (s, 1H), 8.51 (d, 2H, J=8.52 Hz), 8.03 (d, 2H, J=8.56 Hz), 7.42 (m, 1H), 7.37 (d, 1H, J=4.80 Hz), 7.26 (m, 2H), 7.01 (d, 1H, J=4.80 Hz), 6.67 (d, 1H, J=6.72 Hz), 4.15 (m, 2H), 3.70 (m, 4H), 3.31 (s, 3H), 3.13 (m, 5H), 1.13 (d, 3H, J=6.16 Hz).

Sources & evidence

ORD record
ord-7b83a49fa27c403fbfee61d662f0280b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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