1,2,3,4-Tetrahydroquinoline → HCID 19024457, compound

HRID 1033806Notes

Reaction equation

HRID 1033806 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:23](Cl)=[O:24])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[NH:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43][CH2:42][CH2:41]1>C1(C)C=CC=CC=1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:23]([N:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:43][CH2:42][CH2:41]2)=[O:24])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 81531DiisopropylethylamineHCID 19024475HCID 19024475, compound

Product 1

HCID 19024457HCID 19024457, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 100 mg (0.22 mmole) of N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-N-pentylcarbamoyl chloride (from Example 2, Step B), 0.2 mL (1.15 mmole) of N,N-diisopropylethylamine, and 44 mg (0.33 mmole) of 1,2,3,4-tetrahydroquinoline in 2.5 mL of toluene was stirred at 110° C. for two days. After cooling to room temperature, volatiles were removed by rotary evaporation, and the residue was flash chromatographed over silica gel (gradient elution using 10% to 12.5% EtOAc in hexane) to give 81 mg (66%) of the desired product as an oil, homogeneous by TLC (4:1 hexane-EtOAc), FAB-MS m/e 548 (M+1)+.

Workup

  1. customvolatiles were removed by rotary evaporation
  2. customchromatographed over silica gel (gradient elution using 10% to 12.5% EtOAc in hexane)

Sources & evidence

ORD record
ord-70def6782c5646bc8117f38c767ff6f1
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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