1,2-Dichloroethane → HCID 70275424, compound

HRID 365449Notes

Reaction equation

HRID 365449 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 NH4OH) 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 NH4OH)

Sources & evidence

ORD record
ord-1b98a620b8fe4539b4800f19ef6eb150
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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