Toluene → HCID 10255967, compound

HRID 1374792Notes

Reaction equation

HRID 1374792 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[C:5]([CH3:15])[N:6]2[CH2:11][C:12]([OH:14])=[O:13].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C1(C)C=CC=CC=1>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([S:16][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[N:34]3[CH2:33][CH2:32][N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:36][CH2:35]3)[N:6]([CH2:11][C:12]([OH:14])=[O:13])[C:5]=2[CH3:15])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10047207HCID 10047207, compound

Product 1

HCID 10255967HCID 10255967, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a dry flask was charged the product from example 22 part (ii) (1 g), N-tert-Butoxycarbonylpiperazine (0.48 g), Pd2(dba)3 (3 mg), 2,2′-bis(diphenylphosphino)-1,1′-binapthyl Binap (10 mg) and toluene (5 ml). The reaction was heated to 110° C. for 1 hour then allowed to cool. The mixture was diluted with EtOAc, washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified using Flash column chromatography (eluent 25% EtOAc/Hexane then 50% EtOAc/Hexane/1% Acetic acid). Further purification using reverse phase preparative HPLC (eluent MeCN/NH3 (aq)) gave titled compound (0.021 g).

Workup

  1. temperatureto cool
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. customFurther purification

Sources & evidence

ORD record
ord-11678d194163415fbe3278956ef908ef
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

Loading…