1,2-Dichloroethane → HCID 18340693, compound

HRID 2298975Notes

Reaction equation

HRID 2298975 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13](O)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(Cl)CCl.[CH:20]1[CH:25]=[N:24][C:23]2[N:26](O)N=[N:28][C:22]=2[CH:21]=1.C1(N)C=CC=CC=1N>CN(C=O)C.C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[NH:28][C:22]3[C:23]([N:26]=2)=[N:24][CH:25]=[CH:20][CH:21]=3)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 181649HOAtHCID 158961924-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 18340693HCID 18340693, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 69846924Toluene trifluoroacetic acidSolvent

Conditions

Temperature
90 °C

Procedure

Compound AAA was prepared by the following procedure. To a solution of 4-carboxymethyl-cyclohexanecarboxylic acid ethyl ester (10.5 g, 49.0 mmol), EDC (9.4 g, 49.0 mmol) and HOAt (6.7 g, 49.0 mmol) in 80 mL anhydrous DMF was added phenylenediamine (5.3 g, 49.0 mmol) and the reaction mixture stirred for 1 h. The resulting reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc and the organic portion washed 3× with water. The organic layer was dried with MgSO4 and concentrated to yield a yellow oil. The crude material was dissolved in toluene/TFA (1:1 300 mL), heated to 90° C., and stirred overnight. The reaction mixture was then concentrated and purified by column chromatography on silica using EtOAc followed by 90:10:1 CH2Cl2/MeOH/NH4OH to give 4-(1H-imidazo[4,5-b]pyridin-2-ylmethyl)-cyclohexanecarboxylic acid ethyl ester as a colorless oil. Data for cis/trans mixture: mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 287].

Workup

  1. customCompound AAA was prepared by the following procedure
  2. customThe resulting reaction mixture
  3. customwas partitioned between saturated aqueous NaHCO3 and EtOAc
  4. washthe organic portion washed 3× with water
  5. dry with materialThe organic layer was dried with MgSO4
  6. concentrationconcentrated
  7. customto yield a yellow oil
  8. stirringstirred overnight
  9. concentrationThe reaction mixture was then concentrated
  10. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-e396c57a7f8246829d751fdc2251074a
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

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