Water → HCID 86725397, compound

HRID 1503854Notes

Reaction equation

HRID 1503854 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](Cl)=[O:7].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 111276553-methoxy-4-nitro-benzoyl Chloride

Product 1

HCID 86725397HCID 86725397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 39A (13 mmol) in dichloromethane (100 mL) at 0° C. was added slowly tert-butyl piperazine-1-carboxylate (1.06 g, 13 mmol) and triethylamine (3.6 mL). After stirring for 2 hours, water was added slowly and the mixture was extracted with dichloromethane (3×200 mL). The combined organic phase was washed with brine, dried over sodium sulfate, filtered, concentrated and purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to provide the title compound. MS: 388 (M+H+).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×200 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (200-300 mesh)
  7. washeluting with 100/1 dichloromethane/methanol

Sources & evidence

ORD record
ord-e262f7204e2a4cbb93e8b9f710b1fb56
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

Loading…