Ethyl Acetoacetate → (S)-ethyl 4-amino-5-(2-aminobutoxy)-2-methylquinoline-3-carboxylate

HRID 1467093Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:24]#[N:25])=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][C@@H:7]([NH:10]C(=O)OCC1C=CC=CC=1)[CH2:8][CH3:9].O=[C:27]([CH3:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>>[NH2:25][C:24]1[C:3]2[C:2](=[CH:23][CH:22]=[CH:21][C:4]=2[O:5][CH2:6][C@@H:7]([NH2:10])[CH2:8][CH3:9])[N:1]=[C:27]([CH3:34])[C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 86658219(S)-benzyl 1-(3-amino-2-cyanophenoxy)butan-2-ylcarbamate

Product 1

HCID 86658218(S)-ethyl 4-amino-5-(2-aminobutoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from (S)-benzyl 1-(3-amino-2-cyanophenoxy)butan-2-ylcarbamate (Example 97c) and ethyl 3-oxobutanoate as brown solid (75%). MS 318 (MH+).

Sources & evidence

ORD record: ord-c053139d354c4999b57346f1e7f9688a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000054B2

Reaction notes

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