1,2-Dichloroethane → HCID 66611615, compound

HRID 2204724Notes

Reaction equation

HRID 2204724 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[CH:11][C:12]([Cl:18])=[C:13]([CH:17]=1)[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[C:13]([C:14]([N:42]2[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]2)=[O:15])[C:12]([Cl:18])=[CH:11][C:10]=1[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66610949HCID 66610949, compound

Product 1

HCID 66611615HCID 66611615, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(benzyloxy)-4-((benzyloxy)carbonyl)-2-chlorobenzoic acid (may be prepared as described in D74) (500 mg, 1.260 mmol) in N,N-Dimethylformamide (DMF) (5 mL) were added DIPEA (0.660 mL, 3.78 mmol), 1-methylpiperazine (0.182 mL, 1.638 mmol), 1-hydroxy-7-azabenzotriazole (206 mg, 1.512 mmol) and EDC (435 mg, 2.268 mmol). The mixture was stirred at room temperature for 8 hrs. The solvent was removed in vacuo. The residue was redissolved in DCM (10 mL) and washed with water (10 mL), dried over MgSO4 and concentrated in vacuo. Purification by column (Si, Isolute, 10% 2M NH3 in MeOH/DCM) gave the title product as a yellow solid (400 mg, 66% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in DCM (10 mL)
  3. washwashed with water (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by column (Si, Isolute, 10% 2M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-727b14920ca8428eb00ca7d185ac9b7b
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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