Ethyl Acetoacetate → Ethyl 4-amino-5-((4-(isopropylcarbamoyl)cyclohexyl)oxy)-2-methyl-quinoline-3-carboxylate

HRID 2047795Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:21]#[N:22])=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.O=[C:24]([CH3:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[CH2:29]([O:28][C:26]([C:25]1[C:24]([CH3:31])=[N:1][C:2]2[C:3]([C:21]=1[NH2:22])=[C:4]([O:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:13])[NH:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:7]1)[CH:18]=[CH:19][CH:20]=2)=[O:27])[CH3:30]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 667457454-(3-amino-2-cyanophenoxy)-N-isopropylcyclohexanecarboxamide

Product 1

HCID 66746795Ethyl 4-amino-5-((4-(isopropylcarbamoyl)cyclohexyl)oxy)-2-methyl-quinoline-3-carboxylate

Procedure

Prepared as in Example 2a from 4-(3-amino-2-cyanophenoxy)-N-isopropylcyclohexanecarboxamide (Example 45b) and ethyl 3-oxobutanoate as a yellow solid (56%). MS 414 (MH+).

Sources & evidence

ORD record: ord-61ca03fa7b664d3eaf163ad8009c36c5
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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