Isatin → HCID 178444720, compound

HRID 1876255Notes

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].[C:12]12([C:22]([NH:24][NH2:25])=[O:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>>[CH2:2]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[N:25]/[NH:24][C:22]([C:12]23[CH2:21][CH:16]4[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]4)[CH2:19]2)[CH2:13]3)=[O:23])/[C:2]1=[O:3])[CH2:4][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 7054Isatin

HCID 337203adamantane-1-carbohydrazide

Product 1

HCID 178444720HCID 178444720, compoundYield 59%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and adamantanecarbohydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 59%. 1H NMR (DMSO-d6): δ 0.85 (t, J=6.9 Hz, 3H), 1.27 (m, 6H), 1.60-1.65 (m, 2H), 1.72 (s, 6H), 1.91 (s, 6H), 2.05 (s, 3H), 3.75 (t, J=7.2 Hz, 2H), 7.16 (t, J=7.5 Hz, 1H), 7.21 (d, J=7.8 Hz, 1H), 7.46 (t, J=7.8 Hz, 1H), 7.59 (d, J=7.5 Hz, 1H), 13.28 (br s, 1H). 13C NMR (DMSO-d6): δ 14.32 (CH3), 22.44 (CH2), 26.38 (CH2), 27.41 (CH2), 27.85 (CH), 31.31 (CH2), 36.32 (CH), 38.80 (CH2), 39.52 (CH2), 110.59 (CH), 119.75 (C), 121.03 (CH), 123.61 (CH), 131.96 (CH), 143.27 (C═N), 161.39 (C═O). HRMS (ES+) calcd for C25H34N3O2 (M+H+), m/e, 408.2660; found, 408.2646.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-759dce12333144e8ab466be10ce6e329
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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