Ethyl 4-bromobutyrate → HCID 86592045, compound

HRID 1785906Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=3)[N:15]([C:23](=[O:33])[C:24]3[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[C@@H:14]([CH3:34])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH2:35]([O:37][C:38](=[O:74])[CH2:39]CCOC1C=CC(C(N2C3C(=CC=CC=3)[C@H](N(C3C=CC(Cl)=CC=3)C(=O)CC)C[C@@H]2C)=O)=CC=1)[CH3:36].BrCCCC(OCC)=O>>[CH2:35]([O:37][C:38](=[O:74])[CH2:39][O:22][C:18]1[CH:17]=[C:16]2[C:21]([C@H:12]([N:8]([C:9](=[O:11])[CH3:10])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:13][C@H:14]([CH3:34])[N:15]2[C:23](=[O:33])[C:24]2[CH:25]=[CH:26][C:27]([N:30]([CH3:32])[CH3:31])=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)[CH3:36]

Participants

Reactant 3

HCID 76300Ethyl 4-bromobutyrate

HCID 10050736HCID 10050736, compound

HCID 86592022HCID 86592022, compound

Product 1

HCID 86592045HCID 86592045, compound

Procedure

(±)-Cis-[4-[acetyl-(4-chloro-phenyl)-amino]-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-7-yloxy]-acetic acid ethyl ester was prepared from (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-dimethylamino-benzoyl)-7-hydroxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide, following the alkylation conditions described for the synthesis of (±)-cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester, substituting ethyl bromoacetate for ethyl 4-bromobutyrate.

Sources & evidence

ORD record: ord-f15c55a7229a43138f1c1bb39467f81b
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

Loading…