1,2-Dichloroethane → HCID 69075149, compound

HRID 228119Notes

Reaction equation

HRID 228119 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[NH:17](C(OC(C)(C)C)=O)[C@@H:18]([C:27](O)=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:17][C@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:27]([N:13]1[CH2:14][CH2:15][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][N:2]([CH3:16])[CH3:1])[CH2:11][CH2:12]1)=[O:28]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 18713602HCID 18713602, compound

Product 1

HCID 69075149HCID 69075149, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2R)-2-amino-1-(4-{2-[(dimethylamino)methyl]phenyl}piperazinyl)-3-(4-chlorophenyl)propan-1-one was prepared according to the procedure described in Preparation V using dimethyl[(2-piperazinylphenyl)methyl]amine (Step 3) (0.35 g, 1.4 mmol), Boc-p-Cl-D-Phe-OH (Peptech Corp.) (0.53 g, 1.8 mmol) in CH2Cl2 (7 mL), EDC (Aldrich Chemical Company) (0.37 g, 1.9 mmol) and HOBT (used in place of HOAT) (Bachem) (0.27 g, 1.8 mmol). After workup as described in Preparation V, the crude compound was dissolved in CH2Cl2 (10 mL) and treated with TFA (5 mL). After stirring the reaction at RT for 1 h, the solvent was concentrated in vacuo and the residue was partitioned between CH2Cl2 and satd NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give (2R)-2-amino-1-(4-{2-[(dimethylamino)methyl]phenyl}piperazinyl)-3-(4-chlorophenyl)propan-1-one as a yellow oil (0.53 g). MS m/z: 401 (M+H). Calc'd for C22H29ClN4O: 400.94.

Workup

  1. custom(2R)-2-amino-1-(4-{2-[(dimethylamino)methyl]phenyl}piperazinyl)-3-(4-chlorophenyl)propan-1-one was prepared
  2. customdescribed in Preparation V
  3. customAfter workup as described in Preparation V
  4. customthe reaction at RT for 1 h
  5. concentrationthe solvent was concentrated in vacuo
  6. customthe residue was partitioned between CH2Cl2
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8711a5cd38bc492aa07decfe43f5e6ad
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

Loading…