Ethyl Acetoacetate → HCID 66745763, compound

HRID 2047737Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[C:4]#[N:5].O=[C:17]([CH3:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH2:22]([O:21][C:19]([C:18]1[C:17]([CH3:24])=[N:1][C:2]2[C:3]([C:4]=1[NH2:5])=[C:6]([O:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[CH:8][CH:9]=2)=[O:20])[CH3:23]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 66745775HCID 66745775, compound

Product 1

HCID 66745763HCID 66745763, compound

Procedure

Prepared as in Example 2a from 2-amino-6-(neopentyloxy)benzonitrile (Tachdjian, C. et al. PCT Int. Appl. 2008, WO 2008154221) and ethyl 3-oxobutanoate as a white solid (64%). 1H NMR (400 MHz, DMSO-d6) δ 1.06 (s, 9H), 1.32 (t, J=6.8 Hz, 3H), 2.54 (s, 3H), 3.86 (s, 2H), 4.31 (q, J=6.8 Hz, 2H). 6.88-6.91 (m, 1H), 7.22-7.25 (m, 1H), 7.50 (t, J=8.0 Hz, 1H), 8.06 (s, 2H). MS 317 (MH+).

Sources & evidence

ORD record: ord-f187ac15317c43bdb9bab371ade7ce47
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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