1-(4-Nitrophenyl)piperazine → HCID 66711040, compound

HRID 1261951Notes

Reaction equation

HRID 1261951 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.[Cl:51][C:52]1[CH:53]=[CH:54][C:55]([O:70][CH3:71])=[C:56]([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:57]=1>>[Cl:51][C:52]1[CH:53]=[CH:54][C:55]([O:70][CH3:71])=[C:56]([C:58]2[N:66]3[C:61]([CH:62]=[N:63][C:64]([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:65]3)=[CH:60][CH:59]=2)[CH:57]=1

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 66710941HCID 66710941, compound

Product 1

HCID 66711040HCID 66711040, 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 7-(5-Chloro-2-methoxy-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine to afford 19.24 mg of (R)-1-(4-{3-[7-(5-Chloro-2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperazin-1-yl)-propan-2-ol as a lyophilized powder. (M+H)=493.09. 1H NMR (400 MHz, DMSO, d6) δ 9.34 (s, 1H), 8.98 (s, 1H), 7.94 (m, 1H), 7.50 (dd, 1H, J=2.64, 6.24 Hz), 7.39 (d, 1H, J=8.12 Hz), 7.24 (d, 1H, J=8.96 Hz), 7.14 (m, 2H), 7.01 (d, 1H, J=4.68 Hz), 6.93 (d, 1H, J=4.68 Hz), 6.59 (dd, 1H, J=1.80, 6.48 Hz), 4.12 (m, 2H), 3.80 (s, 3H), 3.53 (m, 4H), 3.15 (m, 3H), 3.02 (m, 2H), 1.15 (d, 2H, J=6.16 Hz).

Sources & evidence

ORD record
ord-2488d276e8124bf5b5b384df783008cd
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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