Ethyl Acetoacetate → Ethyl 4-amino-5-(2-(cyclohexanecarboxamido)-2-methylpropoxy)-2-methylquinoline-3-carboxylate

HRID 2047778Notes

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

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 66745570N-(1-(3-amino-2-cyanophenoxy)-2-methylpropan-2-yl)cyclohexanecarboxamide

Product 1

HCID 66747112Ethyl 4-amino-5-(2-(cyclohexanecarboxamido)-2-methylpropoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from N-(1-(3-amino-2-cyanophenoxy)-2-methylpropan-2-yl)cyclohexanecarboxamide (Example 37b) and ethyl 3-oxobutanoate as a bright yellow solid (55%). MS 428 (MH+).

Sources & evidence

ORD record: ord-94124aa05cd545a0b0fcc824618871a3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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