5-Methoxyoxindole → HCID 178487090, compound

HRID 1466254Notes

Reaction equation

HRID 1466254 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[C:22]4[C:17](=[CH:18][C:19]([CH:23]=[C:24]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[NH:26][C:25]5=[O:33])=[CH:20][CH:21]=4)[NH:16][N:15]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH3:34][O:35]C1C=C2C(=CC=1)NC(=O)C2>>[CH3:34][O:35][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:33])[C:24]2=[CH:23][C:19]1[CH:18]=[C:17]2[C:22]([C:14]([C:11]3[CH:12]=[N:13][C:8]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:9][CH:10]=3)=[N:15][NH:16]2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 15142865-MethoxyoxindoleHCID 1784806553-[[3-[6-(4-methylpiperazin-1-yl)-3-pyridinyl]-1H-indazol-6-yl]methylidene]-1H-indol-2-one

Product 1

HCID 178487090HCID 178487090, compound

Procedure

According to the procedure for the synthesis of 3-((3-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazol-6-yl)methylene)indolin-2-one, except substituting 5-methoxyoxindole (28 mg, 0.087 mol), the title compound was prepared as a yellow solid (14.4 mg, 35%). A mixture of (E)- and (Z)-isomers (83:17 by NMR) was obtained. 1H NMR (400 MHz, CD3OD) 8.74 (d, J=2.3 Hz, 1H), 8.14 (dd, J=8.8, 2.3 Hz, 1H), 8.07 (d, J=8.5 Hz, 1H), 7.87 (d, J=10.0 Hz, 2H), 7.49 (d, J=8.3 Hz, 1H), 7.26 (s, 1H), 7.01 (d, J=8.8, 1H), 6.83 (s, 2H), 3.75-3.69 (br. m, 4H), 3.62 (s, 3H), 2.82-2.76 (br. m, 4H), 2.51 (s, 3H); MS ESI 467.2 [M+H]+, calcd for [C27H26N6O2+H]+ 467.21.

Sources & evidence

ORD record
ord-e2d7d4278548479b94378a09826cde0c
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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