1,2-Dichloroethane → HCID 24753121, compound

HRID 1919890Notes

Reaction equation

HRID 1919890 reaction equation
CO[C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[O:12])=[N:6][CH:5]=1.[OH-].[Li+].Cl.[C:35]1([NH2:42])[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH2:41].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C1COCC1.C(Cl)Cl.O.CO>[NH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:42][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:21]3[C:22](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:23]=2)=[O:12])=[N:6][CH:5]=1

Participants

11

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 57611951HCID 57611951, compound

Product 1

HCID 24753121HCID 24753121, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound from Step A above was dissolved in 0.5 mL each of THF, methanol and water then 12.0 mg (0.5 mmol) of lithium hydroxide was added and the solution was stirred for 18 h at rt. The solution was allowed to cool to room temperature and 300 μL of 2 N HCl was added. The solvent was evaporated and the residue was dissolved in 500 μL of DMF. Phenylenediamine (104 mg, 0.500 mmol), EDC (96.7 mg, 0.500 mmol), and HOBt (67.2 mg, 0.500 mmol) were added and the solution was allowed to stir for 18 h. The solution was diluted with 50 mL of CH2Cl2 and washed with 50 mL each of NaHCO3 and brine. The solution was concentrated and purified by reverse phase HPLC to give the desired product. MS cal'd 495 (MH+), exp 495 (MH+).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 500 μL of DMF
  4. stirringto stir for 18 h
  5. washwashed with 50 mL each of NaHCO3 and brine
  6. concentrationThe solution was concentrated
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-44dcb8289efb483cbd10e31565ec20ed
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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