Piperidine → HCID 178487091, compound

HRID 1615368Notes

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]=O)=[CH:20][CH:21]=4)[NH:16][N:15]=3)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[CH2:30]2.N1CCCCC1>CO>[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])/[C:30]/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[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[N:9][CH:10]=3)=[N:15][NH:16]2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A round bottom flask was charged with 3-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-1H-indazole-6-carbaldehyde (26 mg, 0.80 mmol), 5-methoxyoxindole (13 mg, 0.80 mmol), piperidine (0.8 uL, 0.008 mmol) and MeOH (2 mL). The reaction was then heated to 60° C. for 4 hrs. An orange precipitate formed which was further precipitated by cooling to room temperature. The orange solid was then filtered and washed with MeOH (5 mL) giving 9.8 mg, 26% of the title compound. 1H NMR (400 MHz, d6-DMSO) δ 13.46 (s, 1H), 10.44 (s, 1H), 8.97 (s, 2H), 8.18 (d, J=8.5 Hz, 1H), 7.94 (s, 1H), 7.78 (s, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.20 (s, 1H), 6.85 (d, J=10.6 Hz, 1H), 6.80 (d, J=9.0 Hz, 1H), 3.82 (br t, 4H), 3.59 (s, 3H), 2.39 (br t, 4H), 2.23 (s, 3H); MS ESI 468.3 [M+H]+, calcd for [C26H25N7O2+H]+ 468.2.

Workup

customAn orange precipitate formed which
customwas further precipitated
temperatureby cooling to room temperature
filtrationThe orange solid was then filtered
washwashed with MeOH (5 mL)

Sources & evidence

ORD record: ord-4ce08d5e50fa4522b529d48b7daec510
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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