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

HRID 1467013Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:23]#[N:24])=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][CH2:6][C@@H:7]([NH:9]C(=O)OCC1C=CC=CC=1)[CH3:8].O=[C:26]([CH3:33])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[NH2:24][C:23]1[C:3]2[C:2](=[CH:22][CH:21]=[CH:20][C:4]=2[O:5][CH2:6][C@@H:7]([NH2:9])[CH3:8])[N:1]=[C:26]([CH3:33])[C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 86658189(S)-benzyl(1-(3-amino-2-cyanophenoxy)propan-2-yl)carbamate

Product 1

HCID 86658188(S)-ethyl 4-amino-5-(2-aminopropoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from (S)-benzyl (1-(3-amino-2-cyanophenoxy)propan-2-yl)-carbamate (Example 26c) and ethyl 3-oxobutanoate as brown solid. MS 304 (MH+).

Sources & evidence

ORD record: ord-97dfa2de8cae4fd982f2e0aaf650b18a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000054B2

Reaction notes

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