1,2-Dichloroethane → HCID 66920249, compound

HRID 1510081Notes

Reaction equation

HRID 1510081 reaction equation
[Cl:1][C:2]1[N:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[C:9]([C:10]=1[C:11](O)=[O:12])=[CH:8][C:7]([O:14][CH3:15])=[CH:6][CH:5]=2.[N:22]1([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[C:31]([O:30][C:28]([N:22]1[CH2:27][CH2:26][N:25]([C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=3)[N:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:2]=2[Cl:1])=[O:12])[CH2:24][CH2:23]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 181649HOAtHCID 669204422-Chloro-5-methoxy-1-phenyl-1h-indole-3-carboxylic acid

Product 1

HCID 66920249HCID 66920249, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 602 mg (1.99 mmol) of the compound of step 4, tert-butyl 1-piperazinecarboxylate (372 mg, 1.99 mmol), EDC (421 mg, 2.19 mmol) and HOAT (312 mg, 2.29 mmol) in DMF (5 ml) was added NMM (0.66 ml, 5.98 mmol), and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated to give 930 mg of the title compound.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-545ef21366d74c6ab24b574856d56ef4
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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