Sodium Carbonate → Ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875342Notes

Reaction equation

HRID 875342 reaction equation
I[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][C:55]3[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=3)=[CH:49][CH:48]=2)=[C:25]([CH2:27][CH2:28][NH:29][CH:30]2[CH2:39][CH2:38][CH2:37][C:36]3[N:35]=[C:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:33]=[CH:32][C:31]2=3)[CH:26]=1>C(#N)C>[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][C:55]3[CH:56]=[CH:57][C:58]([F:61])=[CH:59][CH:60]=3)=[CH:49][CH:48]=2)=[C:25]([CH2:27][CH2:28][N:29]([CH2:2][CH2:3][C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[CH:30]2[CH2:39][CH2:38][CH2:37][C:36]3[N:35]=[C:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:33]=[CH:32][C:31]2=3)[CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 22639144Methyl 4-(2-iodoethyl)benzoateHCID 86709831Ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

Product 1

HCID 86709833Ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

305 mg (1.05 mmol) of methyl 4-(2-iodoethyl)benzoate and 56 mg (0.53 mmol) of anhydrous sodium carbonate were added to a solution of 200 mg (0.35 mmol) of ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 2, Example 143A) in 3 ml of dry acetonitrile, and the mixture was stirred in a microwave apparatus (Biotage Initiator) at 140° C. for 4 hours. The reaction solution was then cooled and purified directly by preparative HPLC (mobile phase: acetonitrile/water 9:1). This gave 75 mg (0.10 mmol, 29% of theory) of the title compound.

Workup

  1. temperatureThe reaction solution was then cooled
  2. custompurified directly by preparative HPLC (mobile phase: acetonitrile/water 9:1)

Sources & evidence

ORD record
ord-374996487cbc41d1820906337c4344a6
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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