Ethyl Acetoacetate → HCID 66745780, compound

HRID 2169984Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:22]#[N:23])=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.O=[C:25]([CH3:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>>[NH2:23][C:22]1[C:3]2[C:2](=[CH:21][CH:20]=[CH:19][C:4]=2[O:5][CH2:6][CH:7]2[CH2:12][CH2:11][CH:10]([C:13](=[O:14])[NH:15][CH:16]([CH3:18])[CH3:17])[CH2:9][CH2:8]2)[N:1]=[C:25]([CH3:32])[C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 66746014HCID 66746014, compound

Product 1

HCID 66745780HCID 66745780, compound

Procedure

Prepared as in Example 2a from 4-((3-amino-2-cyanophenoxy)methyl)-N-isopropylcyclohexanecarboxamide (Example 126b) and ethyl 3-oxobutanoate as a pale yellow solid (37%). 1H NR (400 MHz, DMSO-d6) δ 1.01 (d, J=6.4 Hz, 6H), 1.32 (t, J=7.2 Hz, 3H), 1.38-1.81 (m, 8H), 1.88 (m, 1H), 2.25 (m, 1H), 2.55 (s, 3H), 3.82 (bro, J=7.6 Hz, 1H), 4.10 (d, J=6.4 Hz, 2H), 4.31 (q, J=7.6 Hz, 2H), 6.93 (d, J=7.6 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 7.50 (m, 2H), 8.09 (s, 2H). MS 428 (MH+).

Sources & evidence

ORD record: ord-6e447e4485764fe395d07e15a03799ba
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09049878B2

Reaction notes

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