Isatin → HCID 178444724, compound

HRID 1522966Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[CH:12]1([C:18]([NH:20][NH2:21])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH2:2]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[N:21]/[NH:20][C:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:19])/[C:2]1=[O:3])[CH2:4][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 7054Isatin

HCID 240039Cyclohexanecarbohydrazide

Product 1

HCID 178444724HCID 178444724, compoundYield 45%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and cyclohexanecarbohydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 45%. 1H NMR (DMSO-d6): δ δ 0.85 (t, J=6.8 Hz, 3H), 1.24-1.83 (m, 19H), 3.74 (t, J=6.9 Hz, 2H), 7.15 (t, J=7.5 Hz, 1H), 7.19 (d, J=7.8 Hz, 1H), 7.45 (t, J=7.8 Hz, 1H), 7.48 (d, J=7.5 Hz, 1H), 7.59 (d, 3H), 12.34 (br s, isomer 1: 50%, 0.5; H), 13.00 (br s, isomer 2: 50%, 0.5; H), both isomer are in the same proportion. 13C NMR (DMSO-d6): δ 14.33(CH3), 22.42 (CH2), 25.48 (CH2), 26.34 (CH2), 25.83 (CH2), 27.37 (CH2), 31.29 (CH2), 39.64 (CH2), 110.52 (CH), 119.78 (C), 123.48 (CH), 131.79 (CH), 143.27 (C═N), (C═O). HRMS (ES+) calcd for C21H30N3O2 (M+H+), m/e, 356.2328. found, 356.2333.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-24b3c32ae9a241a18ee5222a63aa98ba
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079854B2

Reaction notes

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