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

HRID 2169863Notes

Reaction equation

C(OC(=O)[NH:10][C@@H:11]([CH3:23])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[C:15]=1[C:21]#[N:22])C1C=CC=CC=1.O=[C:26]([CH3:33])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[NH2:22][C:21]1[C:15]2[C:16](=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12][C@@H:11]([NH2:10])[CH3:23])[N:20]=[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-21bb49f215664c06a672333ab6cb58c3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09049878B2

Reaction notes

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