Methyl 3-oxovalerate → HCID 66745629, compound

HRID 1466977Notes

Reaction equation

HRID 1466977 reaction equation
[NH2:1][C:2]1[C:3]([C:19]#[N:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]([CH3:15])([CH3:14])[C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9].O=[C:22]([CH2:28][CH3:29])[CH2:23][C:24]([O:26][CH3:27])=[O:25]>>[NH2:20][C:19]1[C:3]2[C:2](=[CH:18][CH:17]=[CH:16][C:4]=2[O:5][CH2:6][C:7]([CH3:15])([CH3:14])[C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH3:13])[N:1]=[C:22]([CH2:28][CH3:29])[C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

3

Reactant 2

HCID 121699Methyl 3-oxovalerateHCID 468336623-(3-Amino-2-cyanophenoxy)-2,2-dimethyl-N-propylpropanamide

Product 1

HCID 66745629HCID 66745629, compound

Procedure

Prepared as in Example 2a from 3-(3-amino-2-cyanophenoxy)-2,2-dimethyl-N-propylpropan-amide (Tachdjian, C. et al. PCT Int. Appl. 2008, WO 2008154221) and methyl 3-oxopentanoate as a yellow solid (17%). 1H NMR (400 MHz, DMSO-d6) δ 0.75 (t, J=8.0 Hz, 3H), 1.17 (t, J=8.0 Hz, 3H), 1.26 (s, 6H), 1.40 (m, 2H), 2.84 (q, J=8.0 Hz, 2H), 3.04 (q, J=8.0 Hz, 2H), 3.85 (s, 3H), 4.13 (s, 2H), 6.88 (d, J=8.0 Hz, 1H), 7.27 (dd, J=8.0 Hz, 1H), 7.51 (t, J=8.0 Hz, 1H), 7.81 (m, 3H). MS 388 (MH+).

Sources & evidence

ORD record
ord-9663a55f042741c6bbbc91f8acca103c
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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