1,2-Dichloroethane → HCID 70275424, compound

HRID 399123Notes

Reaction equation

HRID 399123 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][C@@H:9]([C:11](=[O:29])[NH:12][CH2:13][CH2:14][C:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:8][NH:7][CH2:6]1)=[O:4].[C:30]1([CH:36]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:37](O)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1C=C2C(N(O)N=NC2=CC=1)=O.C(Cl)CCl.CCN(CC)CC>CN(C=O)C>[C:40]1([CH:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:37]([N:7]2[CH2:8][C@H:9]([C:11](=[O:29])[NH:12][CH2:13][CH2:14][C:15]3[N:19]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=4)[CH:18]=[N:17][CH:16]=3)[CH2:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]2)=[O:38])[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 70274442HCID 70274442, compound

Product 1

HCID 70275424HCID 70275424, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis-3-Methoxycarbonyl-5-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine (86.8 mg, 0.219 mmol) (EXAMPLE 2, Step A) diphenyl acetic acid (302 mg, 1.42 mmol), HOOBT (54.3 mg, 0.328 mmol), EDC (63 mg, 0.328 mmol), and Et3N (392 uL, 5.34 mmol) were dissolved in DMF (4 mL) and stirred at ambient temperature for 5 days. The solution was concentrated, the residue was taken up in EtOAc, washed with sat. NaHCO3 solution, water, and brine. The organics were dried (MgSO4), concentrated, and chromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4 OH) to give the title compound. FAB MS=590 (M+1)

Workup

  1. concentrationThe solution was concentrated
  2. washwashed with sat. NaHCO3 solution, water, and brine
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4 OH)

Sources & evidence

ORD record
ord-f27a6fb777024270b0dfd4a5b3601138
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

Loading…