1,2-Dichloroethane → HCID 21083982, compound

HRID 347907Notes

Reaction equation

HRID 347907 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]2[S:14][C:15]([C:23](O)=[O:24])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:5]=2[CH:4]=[CH:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>C(Cl)Cl>[CH3:40][N:41]1[CH2:46][CH2:45][N:44]([C:23]([C:15]2[S:14][C:6]3[N:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2](=[O:1])[CH:3]=[CH:4][C:5]=3[C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:24])[CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 21083991HCID 21083991, compound

Product 1

HCID 21083982HCID 21083982, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of the compound of Example 59 (100 mg, 0.29 mmol) in DCM (2 mL) was added EDC (67 mg, 0.348 mmol) and HOBT (43 mg, 0.32 mmol) and the mixture stirred at r.t. for 15 minutes. A solution N-methyl piperazine (28 mg, 0.32 mmol) in DCM (0.5 mL) was added and the reaction stirred at r.t. for 18 h. The reaction mixture was diluted with DCM (10 mL), washed with water (2×5 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica (0–20% THF in DCM) to give the title compound as an off-white solid (82 mg). δH (DMSO-d6) 7.67 (1H, dd, J 10, 1 Hz), 7.62–7.52 (3H, m), 7.51–7.40 (5H, m), 7.35–7.31 (2H, m), 6.51 (1H, dd, J 10, 1 Hz), 2.44 (8H, m), 1.88 (3H, s). LCMS (ES+) RT 2.18 minutes, 430 (M+H)+.

Workup

  1. stirringthe reaction stirred at r.t. for 18 h
  2. washwashed with water (2×5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica (0–20% THF in DCM)

Sources & evidence

ORD record
ord-c13713227cf74c83b47fad986e38698a
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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