Piperidine → HCID 178474018, compound

HRID 1615235Notes

Reaction equation

[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12](=[O:14])[CH3:13])[CH:8]=2)[NH:3]1.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH:24]=O)[CH:22]=2)[CH:17]=[N:16]1.N1CCCCC1>CO>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21](/[CH:24]=[C:10]3/[C:2](=[O:1])[NH:3][C:4]4[C:9]/3=[CH:8][C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=4)[CH:22]=2)[CH:17]=[N:16]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of N-(2-oxoindolin-5-yl)acetamide (19 mg, 0.1 mmol) was added 1H-indazole-6-carbaldehyde (16 mg, 0.12 mmol), piperidine (2 uL, 0.011 mmol) and MeOH (2 mL). The reaction was then heated to 85° C. for 30 min. The MeOH was removed in vacuo and the solid triturated with ether to give 11 mg, 34% of the title compound as an orange solid. 1H NMR (400 MHz, CD3OD) δ 8.13 (s, 1H), 8.06 (s, 1H), 7.92-7.88 (m, 2H), 7.84 (s, 1H), 7.49 (d, J=8.6 Hz, 1H), 7.35 (d, 1H), 6.88 (d, J=8.3 Hz, 1H), 2.04 (s, 3H); MS ESI 319.1 [M+H]+, calcd for [C18H17N5O3S+H]+ 319.11.

Workup

customThe MeOH was removed in vacuo
customthe solid triturated with ether

Sources & evidence

ORD record: ord-45484cef41414c608c90329cb4c9b9a4
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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