Ethyl Acetoacetate → Ethyl 4-amino-5-(3-(cyclopentylamino)-2,2-dimethyl-3-oxopropoxy)-2-methylquinoline-3-carboxylate

HRID 2047758Notes

Reaction equation

HRID 2047758 reaction equation
[NH2:1][C:2]1[C:3]([C:21]#[N:22])=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH2:6][C:7]([CH3:17])([CH3:16])[C:8]([NH:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:9].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][CH2:6][C:7]([CH3:17])([CH3:16])[C:8]([NH:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:9])[CH:18]=[CH:19][CH:20]=2)=[O:27])[CH3:30]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 667459063-(3-amino-2-cyanophenoxy)-N-cyclopentyl-2,2-dimethylpropanamide

Product 1

HCID 66745905Ethyl 4-amino-5-(3-(cyclopentylamino)-2,2-dimethyl-3-oxopropoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from 3-(3-amino-2-cyanophenoxy)-N-cyclopentyl-2,2-dimethylpropanamide (Example 29b) and ethyl 3-oxobutanoate as a bright yellow solid (62%). 1H NMR (400 MHz, DMSO-d6) δ 1.26 (s, 6H), 1.34 (t, J=8.0 Hz, 3H), 1.40-1.46 (m, 4H), 1.57-1.59 (m, 2H), 1.74-1.77 (m, 2H), 2.57 (s, 3H), 4.09 (q, J=4.0 Hz, 1H), 4.15 (s, 2H), 4.33 (q, J=8.0 Hz, 2H), 6.89 (d, J=4.0 Hz, 1H), 7.26 (dd, J=8.0 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.56 (s, 1H), 8.09 (brs, 2H). MS 414 (MH+).

Sources & evidence

ORD record
ord-21e97528093444dfb0baa1910960f595
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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