Pyridine → (4-{4-[5-(4-Trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 76069Notes

Reaction equation

HRID 76069 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.N1C=CC=CC=1.[F:31][C:32]([F:44])([F:43])[C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:39]([C:36]4[CH:35]=[CH:34][C:33]([C:32]([F:31])([F:43])[F:44])=[CH:38][CH:37]=4)(=[O:41])=[O:40])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 66615773Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

Product 1

HCID 66615794(4-{4-[5-(4-Trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.300 g (0.925 mmol) of {4-[4-(5-Amino-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester, and 8 mL of dichloromethane was added 0.112 mL (1.39 mmol) of pyridine, 0.271 g (1.11 mmol) of 4-Trifluoromethyl-benzenesulfonyl chloride and 0.004 g (0.0277 mmol) DMAP. The dark orange solution was stirred at r.t. for 4 h. The mixture was extracted with dichloromethane, then washed with water, 1 N HCl, and brine. Dried with Na2SO4. Purified on silica gel (EtOAc/Heptane, 9:1 to 6:4) to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d6) 0.99-1.10 (m, 2H) 1.34-1.46 (m, 2H) 1.71-1.82 (m, 5H) 2.14 (d, J=6.82 Hz, 2H) 2.39 (tt, J=−12.16, 3.25 Hz, 1H) 3.57 (s, 3H) 7.16 (d, J=8.34 Hz, 2H) 7.54 (dd, J=2.53, 1.77 Hz, 2H) 7.61 (d, J=8.34 Hz, 2H) 7.73 (d, J=8.34 Hz, 2H) 7.78 (d, J=8.08 Hz, 2H) 8.14 (dd, J=2.27, 1.01 Hz, 1′H).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washwashed with water, 1 N HCl, and brine
  3. dry with materialDried with Na2SO4
  4. customPurified on silica gel (EtOAc/Heptane, 9:1 to 6:4)

Sources & evidence

ORD record
ord-e5bddf4ad8334726b0cd069059505c3b
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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