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

HRID 875348Notes

Reaction equation

HRID 875348 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]([F:63])([F:62])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]2[CH:61]=[CH:60][C:33]([CH2:34][O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH2:42][CH2:43][NH:44][CH:45]3[CH2:54][CH2:53][CH2:52][C:51]4[N:50]=[C:49]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:48]=[CH:47][C:46]3=4)=[CH:32][CH:31]=2)=[CH:24][CH:23]=1>C(#N)C>[CH3:11][O:10][C:8]([C:7]1[CH:12]=[CH:13][C:4]([CH2:3][CH2:2][N:44]([CH2:43][CH2:42][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[O:35][CH2:34][C:33]2[CH:32]=[CH:31][C:30]([CH2:29][CH2:28][C:25]3[CH:26]=[CH:27][C:22]([C:21]([F:63])([F:20])[F:62])=[CH:23][CH:24]=3)=[CH:61][CH:60]=2)[CH:45]2[CH2:54][CH2:53][CH2:52][C:51]3[N:50]=[C:49]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:48]=[CH:47][C:46]2=3)=[CH:5][CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 22639144Methyl 4-(2-iodoethyl)benzoateHCID 86709837Ethyl 5-[(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

Product 1

HCID 86709838Ethyl 5-[{2-[4-(methoxycarbonyl)phenyl]ethyl}(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}-benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

300 mg (1.04 mmol) of methyl 4-(2-iodoethyl)benzoate and 55 mg (0.52 mmol) of anhydrous sodium carbonate were added to a solution of 208 mg (0.35 mmol) of ethyl 5-[(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 2, Example 155A) in 3 ml of dry acetonitrile, and the mixture was stirred in a microwave apparatus (Biotage Initiator) at 140° C. for 4 h. The reaction solution was then cooled and purified directly by preparative HPLC (mobile phase: acetonitrile/water 9:1). This gave 102 mg (0.13 mmol, 39% 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-08f2847c6fb34341954d33c8a9eb72b1
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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