3-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazole-6-carbaldehyde → 3-[[3-[6-(4-methylpiperazin-1-yl)-3-pyridinyl]-1H-indazol-6-yl]methylidene]-1H-indol-2-one

HRID 447292Notes

Reaction equation

HRID 447292 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[C:11]3/[C:12](=[O:20])[NH:13][C:14]4[C:19]/3=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:8]=2)[CH:3]=[N:2]1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[N:33]=[CH:32][C:31](C3C4C(=CC(C=O)=CC=4)NN=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1>>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([C:28]2[N:33]=[CH:32][C:31]([C:3]3[C:4]4[C:9](=[CH:8][C:7]([CH:10]=[C:11]5[C:19]6[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=6)[NH:13][C:12]5=[O:20])=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[CH:30][CH:29]=2)[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 866519683-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazole-6-carbaldehydeHCID 178517060(3E)-3-(1H-indazol-6-ylmethylidene)-1H-indol-2-one

Product 1

HCID 1784806553-[[3-[6-(4-methylpiperazin-1-yl)-3-pyridinyl]-1H-indazol-6-yl]methylidene]-1H-indol-2-one

Procedure

According to the procedure for the synthesis of (E)-3-((1H-indazol-6-yl)methylene)indolin-2-one, except substituting 3-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazole-6-carbaldehyde (40 mg, 0.12 mol), the title compound was prepared as a yellow solid (4.9 mg, 9%). A mixture of (E)- and (Z)-isomers (79:21 by NMR) was obtained. 1H NMR (400 MHz, DMSO-d6) δ 13.34 (br. s, 1H), 10.64 (br. s, 1H), 8.76 (d, J=2.3 Hz, 1H), 8.14 (dd, J=8.8, 2.5 Hz, 2H), 7.91 (s, 1H), 7.79 (s, 1H), 7.62 (d, J=7.8, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.24 (t, J=7.5 Hz, 1H), 6.99 (d, J=9.0 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H), 6.85 (t, J=7.3 Hz, 1H), 3.57 (t, J=4.5 Hz, 4H), 2.42 (t, J=5.0 Hz, 4H), 2.23 (s, 3H); MS ESI 437.2 [M+H]+, calcd for [C26H24N6O+H]+ 437.20.

Sources & evidence

ORD record
ord-77b2d128d4c3469d95047856157c3c01
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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