1,2-Dichloroethane → N1-(6-Indolylcarbonyl)-N2-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]-1,2-benzenediamine

HRID 842382Notes

Reaction equation

HRID 842382 reaction equation
C(OC([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=O)[CH:18]=2)[CH:13]=[CH:12]1)=O)C1C=CC=CC=1.[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH:32]([CH2:35][O:36][C:37]([NH:39][C:40]3[C:41]([NH2:46])=[CH:42][CH:43]=[CH:44][CH:45]=3)=[O:38])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1.C(Cl)CCl.C(OCC)(=O)C>CN(C=O)C.O>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([NH:46][C:41]3[C:40]([NH:39][C:37]([O:36][CH2:35][CH:32]4[CH2:31][CH2:30][N:29]([C:26]5[CH:25]=[CH:24][N:23]=[CH:28][CH:27]=5)[CH2:34][CH2:33]4)=[O:38])=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:22])[CH:18]=2)[CH:13]=[CH:12]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 10829995N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamineHCID 155430401-Benzyloxycarbonyl-6-indolecarboxylic acid

Product 1

HCID 15543028N1-(6-Indolylcarbonyl)-N2-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]-1,2-benzenediamineYield 8.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzyloxycarbonyl-6-indolecarboxylic acid (452 mg, 1.53 mmol), N1-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]-1,2-benzenediamine (500 mg, 1.53 mmol), and EDC (294 mg, 1.53 mmol) in DMF (2.5 mL) was allowed to stir overnight (about 18 h). The mixture was poured into ethyl acetate and H2O, the aqueous layer was washed with EtOAc (3×), and the combined organic extracts were washed with 1 N NaOH (2×), H2O, brine, and dried (K2CO3). Concentration and purification of the residue by flash chromatography (SiO2) followed by recrystallization (MeOH/ether) yielded 60 mg (8%) of the title compound.

Workup

  1. washthe aqueous layer was washed with EtOAc (3×)
  2. washthe combined organic extracts were washed with 1 N NaOH (2×), H2O, brine
  3. dry with materialdried (K2CO3)
  4. concentrationConcentration and purification of the residue by flash chromatography (SiO2)
  5. customfollowed by recrystallization (MeOH/ether)

Sources & evidence

ORD record
ord-c963b8a5dfb846f4aa71539f3efd7a53
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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