1,2-Dichloroethane → HCID 18783765, compound

HRID 1108669Notes

Reaction equation

HRID 1108669 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH:47]([C:50](O)=[O:51])[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].C(Cl)CCl>CN(C=O)C>[F:19][C:2]([F:1])([F:18])[C:3]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:17]=[CH:16][C:14]([NH:15][C:50]([CH:47]3[CH2:48][CH2:49][N:44]([C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:43])[CH2:45][CH2:46]3)=[O:51])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 17047043HCID 17047043, compound

Product 1

HCID 18783765HCID 18783765, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1-N-trifluoroacetyl-4-piperazinyl)aniline (3.0 g, 9.9 mmol), Et3N (2.2 mL, 19 mmol), HOBt (1.5 g, 9.9 mmol), 1-t-butyloxycarbonyl-4-carboxypiperidine (2.3 g, 9.9 mmol) and EDC (1.9 g, 9.9 mmol) in DMF (15 mL) was stirred at RT for 18 hr. Solution was concentrated and the residue was dissolved in EtOAc. EtOAc was washed with: H2O, 5% citric acid (2×), water, 5% NaHCO3 (2×), water and brine. EtOAc was concentrated to givethe title compound (4.35 g, 91%). MS (ES) m/e 485 [M+H]+.

Workup

  1. concentrationSolution was concentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washEtOAc was washed with: H2O, 5% citric acid (2×), water, 5% NaHCO3 (2×), water and brine
  4. concentrationEtOAc was concentrated

Sources & evidence

ORD record
ord-4732ae3379a8480b86e9fd5afc2929b7
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

Loading…