Piperidine → HCID 178517048, compound

HRID 1615277Notes

Reaction equation

[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=O)=[CH:15][CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29].N1CCCCC1>CO>[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][C:14](/[CH:18]=[C:22]3/[C:21](=[O:29])[NH:20][C:28]4[C:23]/3=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:15][CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (E)-3-styryl-1H-indazole-6-carbaldehyde (27 mg, 0.109 mmol) and oxindole (15 mg, 0.109 mmol) in MeOH (1.0 mL) was treated with piperidine (1 uL. 0.011 mmol) and the reaction stirred at 60° C. for 4 hours. The MeOH was removed and the residue purified by prep-HPLC to give 4.7 mg, 12% of a yellow powder. 1H NMR (400 MHz, CD3OD) δ 8.26 (d, J=8.38 Hz, 2H), 7.91-7.86 (m, 2H), 7.71-7.64 (m, 3H), 7.60-7.49 (m, 2H), 7.42 (t, J=7.41 Hz, 2H), 7.31 (t, J=7.49 Hz, 1H), 7.26 (t, J=7.89 Hz, 1H), 6.94 (d, J=7.75 Hz, 1H), 6.89 (t, J=6.86 Hz, 1H); MS ESI 364.2 [M+H]+, calcd for [C24H17N3O+H]+ 364.14.

Workup

customThe MeOH was removed
customthe residue purified by prep-HPLC

Sources & evidence

ORD record: ord-8741d4f9efa74ff6b17473e36d262aae
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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