Ethyl Acetoacetate → HCID 66745973, compound

HRID 1467031Notes

Reaction equation

HRID 1467031 reaction equation
[NH2:1][C:2]1[C:3]([C:26]#[N:27])=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8]1.O=[C:29]([CH3:36])[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>>[NH2:27][C:26]1[C:3]2[C:2](=[CH:25][CH:24]=[CH:23][C:4]=2[O:5][CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[N:1]=[C:29]([CH3:36])[C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 66746517HCID 66746517, compound

Product 1

HCID 66745973HCID 66745973, compound

Procedure

Prepared as in Example 2a from benzyl 4-((3-amino-2-cyanophenoxy)methyl)piperidine-1-carboxylate (Example 35c) and ethyl 3-oxobutanoate as an orange solid (25%). 1H NMR (400 MHz, DMSO-d6) δ 1.29-1.37 (m, 5H), 1.77-1.80 (m, 2H), 2.07 (brs, 1H), 2.53 (s, 3H), 2.55-2.65 (m, 3H), 3.06-3.09 (m, 2H), 4.06 (d, J=8.0 Hz, 2H), 4.32 (q, J=8.0 Hz, 2H), 6.92 (d, J=8.0 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 7.51 (t, J=8.0 Hz, 1H), 8.08 (s, 2H). MS 344 (MH+).

Sources & evidence

ORD record
ord-8dd4d3cd83ef4a1eb543306042d0e951
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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