Ethyl Acetoacetate → Ethyl 4-amino-5-((4-(isonicotinamido)cyclohexyl)-methoxy)-2-methylquinoline-3-carboxylate

HRID 2169952Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:25]#[N:26])=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:9][CH2:8]1.O=[C:28]([CH3:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[NH2:26][C:25]1[C:3]2[C:2](=[CH:24][CH:23]=[CH:22][C:4]=2[O:5][CH2:6][CH:7]2[CH2:8][CH2:9][CH:10]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:11][CH2:12]2)[N:1]=[C:28]([CH3:35])[C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 66745739N-(4-((3-Amino-2-cyanophenoxy)methyl)cyclohexyl)isonicotinamide

Product 1

HCID 66746629Ethyl 4-amino-5-((4-(isonicotinamido)cyclohexyl)-methoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from N-(4-((3-Amino-2-cyanophenoxy)methyl)cyclohexyl)isonicotinamide (Example 108b) and ethyl 3-oxobutanoate as a yellow solid (25%). MS 463 (MH+).

Sources & evidence

ORD record: ord-41da6bf19a8e45f3b0fabe78eee93613
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09049878B2

Reaction notes

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