1,2-Dichloroethane → HCID 59184935, compound

HRID 1943324Notes

Reaction equation

HRID 1943324 reaction equation
[OH:1][C@:2]1([C:43](O)=[O:44])[CH2:19][C@H:18]([O:20][C@@H:21]2[O:35][C@@H:34]([CH3:36])[C@H:24]3[O:25][C@H:26]4[N:31]([C@H:23]3[CH2:22]2)[CH2:30][CH2:29][O:28][C@@H:27]4[O:32][CH3:33])[C:17]2[C:4](=[C:5]([OH:42])[C:6]3[C:7](=[O:41])[C:8]4[C:13]([C:14](=[O:38])[C:15]=3[C:16]=2[OH:37])=[C:12]([O:39][CH3:40])[CH:11]=[CH:10][CH:9]=4)[CH2:3]1.C(N(CC)CC)C.[NH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>ClCCl>[OH:42][C:5]1[C:4]2[CH2:3][C@@:2]([OH:1])([C:43]([N:53]3[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]3)=[O:44])[CH2:19][C@H:18]([O:20][C@@H:21]3[O:35][C@@H:34]([CH3:36])[C@H:24]4[O:25][C@H:26]5[N:31]([C@H:23]4[CH2:22]3)[CH2:30][CH2:29][O:28][C@@H:27]5[O:32][CH3:33])[C:17]=2[C:16]([OH:37])=[C:15]2[C:6]=1[C:7](=[O:41])[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([O:39][CH3:40])[C:13]=1[C:14]2=[O:38]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 4837PiperazineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 59184937HCID 59184937, compound

Product 1

HCID 59184935HCID 59184935, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 56 (9 mg) in anhydrous dichloromethane (5 ml) under argon atmosphere, anhydrous triethylamine (1.6 mg, 0.0158 mmol), piperazine (3.6 mg, 0.0424 mmol), HOBt (2.1 mg, 0.0158 mmol) and EDC (3.0 mg, 0.0158 mmol) were added. The reaction mixture was stirred at room temperature over night. The solvent was evaporated under vacuum and the residue was then purified by flash column chromatography (DCM/MeOH/AcOH/H2O 45/4/1/0.5) on silica gel (230-400 mesh). The product obtained was dissolved in DCM and washed with satd. NaHCO3 (x2) and water (x2). The organic solvent was evaporated under vacuum to afford 5.0 mg of 57. MS (ESI): 696 [M+H]+. Retention time=4.01 min (method 1, Example 3b).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was then purified by flash column chromatography (DCM/MeOH/AcOH/H2O 45/4/1/0.5) on silica gel (230-400 mesh)
  3. customThe product obtained
  4. washwashed with satd
  5. customThe organic solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-c485e531c9dc45008b6287d61e95a9ab
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

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