Triethylamine → 2-(3-((4-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)phenoxy)ethyl methanesulfonate

HRID 2175290Notes

Reaction equation

HRID 2175290 reaction equation
[CH3:1][C:2]1[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][OH:35])[CH:27]=4)[CH:24]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].[CH3:41][S:42](Cl)(=[O:44])=[O:43].C(N(CC)CC)C>C(Cl)Cl>[CH3:41][S:42]([O:35][CH2:34][CH2:33][O:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([CH2:25][N:23]2[CH:24]=[C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[CH2:13][CH2:12][CH2:11][N:10]4[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][O:4][C:3]3[CH:36]=[CH:37][CH:38]=[C:39]([CH3:40])[C:2]=3[CH3:1])[CH:21]=[N:22]2)[CH:27]=1)(=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 709826674-(2,3-Dimethylphenoxy)-1-(5-(1-(3-(2-hydroxyethoxy)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

Product 1

HCID 867125972-(3-((4-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)phenoxy)ethyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2,3-dimethylphenoxy)-1-(5-(1-(3-(2-hydroxyethoxy)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one (0.07 g, 0.13 mmol) in CH2Cl2 (2 mL) at 0° C. was added methanesulfonyl chloride (0.019 g, 0.17 mmol) and triethylamine (0.029 mL, 0.21 mmol) dropwise. The reaction mixture was stirred at 0° C. for 2 h and then quenched with saturated NaHCO3. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with 1 N HCl, saturated NaHCO3, and brine, dried and concentrated to afford the title compound (80 mg, 100%). LCMS, [M+H]+=618.4.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1 N HCl, saturated NaHCO3, and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ad233a02843645ca8bdc73cb1da29ab8
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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