Potassium Carbonate → HCID 68917893, compound

HRID 1785975Notes

Reaction equation

HRID 1785975 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:35]=[CH:34][C:9]([C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([N:22]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:23](=[O:25])[CH3:24])[CH2:14][C@@H:13]2[CH3:33])=[O:11])=[CH:8][CH:7]=1.Br[C:37](C)(C)[C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:23]([N:22]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C@H:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]([C:10]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:37][C:38]([OH:40])=[O:39])=[CH:35][CH:34]=2)=[O:11])[C@@H:13]([CH3:33])[CH2:14]1)(=[O:25])[CH3:24].[CH2:41]([O:40][C:38](=[O:39])[CH2:37][NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([N:22]([C:23](=[O:25])[CH3:24])[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH2:14][C@@H:13]2[CH3:33])=[O:11])=[CH:34][CH:35]=1)[CH3:42]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 58859953HCID 58859953, compound2×

Product 2

HCID 57780740HCID 57780740, compoundHCID 68917893HCID 68917893, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

{[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic acid was prepared from (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide. (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (0.032 g, 0.065 mmol) was dissolved in dimethylformamide, ethyl bromoisobutyrate (0.05 mL, 0.26 mmol) and potassium carbonate (0.018 g, 0.13 mmol) were added. The reaction was heated to 50° C. for 17 h. The reaction was concentrated down and purified using 50% ethyl acetate/50% hexane to 100% ethyl acetate to give 0.007 g, 12% yield of {[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic ethyl ester.

Workup

  1. concentrationThe reaction was concentrated down
  2. custompurified

Sources & evidence

ORD record
ord-114dec0569914f41baf939b57f2aa16f
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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