1,2-Dichloroethane → HCID 178522834, compound

HRID 2298977Notes

Reaction equation

HRID 2298977 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[CH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[F:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38]>CN(C=O)C>[F:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37][NH:38][C:17]([C@H:14]1[CH2:13][CH2:12][C@@H:11]([CH2:10][C:2]2[NH:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)[CH2:16][CH2:15]1)=[O:19]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 666492-FluorobenzylamineHCID 181649HOAtHCID 18378997HCID 18378997, compound

Product 1

HCID 178522834HCID 178522834, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1H-imidazo[4,5-b]pyridin-2-ylmethyl)-cyclohexanecarboxylic acid (Compound AAB) (275 mg, 1.05 mmol), EDC (200 mg, 1.05 mmol) and HOAt (142 mg, 1.05 mmol) in anhydrous DMF (4 mL) was added 2-fluorobenzylamine (131 mg, 1.05 mmol) and the resulting reaction mixture was stirred for 1 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc and the organic layer washed 2× with water. The EtOAc was dried with MgSO4 and concentrated to give a yellow solid. Preparative chromatography eluting with chloroform:methanol gave the cis 4-(1H-imidazo[4,5-b]pyridin-2-ylmethyl)-cyclohexanecarboxylic acid 2-fluoro-benzylamide as a white solid: mass spectrum m/z 367 [(M+H)+; calcd for C21H24N4OF: 366].

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. washthe organic layer washed 2× with water
  4. dry with materialThe EtOAc was dried with MgSO4
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. washPreparative chromatography eluting with chloroform

Sources & evidence

ORD record
ord-4e148143178d4fa6b7dbb746d7f2ddf4
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

Loading…