Diethyl acetonedicarboxylate → HCID 66745949, compound

HRID 2047858Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:3]=1[C:4]#[N:5].O=[C:19]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH2:30]([O:29][C:27]([C:26]1[C:19]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:1][C:2]2[C:3]([C:4]=1[NH2:5])=[C:6]([CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:7]=[CH:8][CH:9]=2)=[O:28])[CH3:31]

Participants

Reactant 2

HCID 66045Diethyl acetonedicarboxylate

HCID 66746378HCID 66746378, compound

Product 1

HCID 66745949HCID 66745949, compound

Procedure

Prepared as in Example 2a from 2-amino-6-(2-cyclohexylethyl)benzonitrile (Example 113b) and diethyl 3-oxopentanedioate as an orange solid (33%). 1H NMR (400 MHz, DMSO-d6) δ 0.87-0.96 (m, 2H), 1.14-1.22 (m, 7H), 1.27-1.32 (m, 4H), 1.47-1.52 (m, 2H), 1.61-1.68 (m, 4H), 1.74-1.77 (m, 2H), 3.21-3.25 (m, 2H), 4.03 (s, 2H), 4.09 (q, J=8.0 Hz, 2H), 4.27 (q, J=8.0 Hz, 2H), 7.27 (t, J=4.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 2H), 7.63 (brs, 2H). MS 413 (MH+).

Sources & evidence

ORD record: ord-9b0e449a672245f28c7b0306b186c264
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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