2-Methoxyethanol → HCID 15005371, compound

HRID 1088661Notes

Reaction equation

HRID 1088661 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[C:32]4[CH:31]=[CH:30][N:29]=[CH:28][C:27]=4[N:26]=[C:25]3[CH3:33])=[CH:20][CH:19]=2)=[C:9]1[C:34]([O:36][CH2:37][CH3:38])=[O:35].C(C1C=C(C(C)C)C=C(C(C)C)C=1S(Cl)(=O)=O)(C)C.[CH3:58][O:59][CH2:60][CH2:61]O>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:61][CH2:60][O:59][CH3:58])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[C:32]4[CH:31]=[CH:30][N:29]=[CH:28][C:27]=4[N:26]=[C:25]3[CH3:33])=[CH:22][CH:23]=2)=[C:9]1[C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 15005366HCID 15005366, compound

Product 1

HCID 15005371HCID 15005371, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (±)-4-(2-chlorophenyl)-1,4-dihydro-3-ethoxycarbonyl-6-methyl-2-[4-(2-methylimidazo[4,5-c]pyridin-1-yl)phenyl]pyridine-5-carboxylic acid (see Example 10) (270 mg, 0.5 mmol), 2,4,6-triisopropylbenzenesulphonyl chloride (377 mg, 1.25 mmol) and 4-dimethylaminopyridine (152 mg, 1.25 mmol) in dry dichloromethane (10 ml) was stirred under a nitrogen atmosphere at room temperature for 3 hours. 2-Methoxyethanol (1.0 ml) was added and the solution was stirred at room temperature for 20 hours. The mixture was concentrated under reduced pressure, the residue was dissolved in excess 0.5M hydrochloric acid and washed with ether (2×30 ml). The aqueous solution was basified with excess saturated aqueous sodium bicarbonate and extracted with dichloromethane (4×30 ml). The combined organic extracts were dried (MgSO4), concentrated, and purified by flash chromatography on silica gel (eluting with 10:1 ethyl acetate/triethylamine) to give, after combination and evaporation of appropriate fractions, the title compound, (93 mg), m.p. 195°-196° C.

Workup

  1. stirringthe solution was stirred at room temperature for 20 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in excess 0.5M hydrochloric acid
  4. washwashed with ether (2×30 ml)
  5. extractionextracted with dichloromethane (4×30 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica gel (eluting with 10:1 ethyl acetate/triethylamine)
  9. customto give
  10. customafter combination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-b838d0679824470c96394277102e8b8c
Source dataset
uspto-grants-1990_10
Patent number
US04963560

Reaction notes

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