1,2-Dichloroethane → HCID 25216170, compound

HRID 1466515Notes

Reaction equation

HRID 1466515 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:5]2.[OH:24][CH2:25][C:26](O)=[O:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:27][CH2:26][C:25]([N:15]1[CH2:14][CH2:13][CH:12]([NH:11][C:9]2[CH:10]=[C:2]([CH3:1])[CH:3]=[C:4]3[C:8]=2[NH:7][C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5]3)[CH2:17][CH2:16]1)=[O:24]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 757Glycolic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 25216168HCID 25216168, compound

Product 1

HCID 25216170HCID 25216170, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5-Methyl-2-phenyl-1H-indol-7-yl)-piperidin-4-yl-amine (305 mg, 1 mmol) prepared in Example 90 was dissolved in DMF (5 mL). Hydroxyacetic acid (76 mg, 1 mmol), EDC (232 mg, 1.3 mmol), HOBT (229 mg, 1.5 mmol) and Et3N (280 uL, 2 mmol) were added thereto, and the mixture was stirred for 4 h at room temperature. After completion of the reaction, saturated aqueous NaHCO3 solution was added to the reaction mixture, which was then extracted with EtOAc, washed with saturated aqueous NaCl solution and 1N HCl, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound.

Workup

  1. additionwas added to the reaction mixture, which
  2. extractionwas then extracted with EtOAc
  3. washwashed with saturated aqueous NaCl solution and 1N HCl
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c4a192146d884d45b3595ad9d7347e9d
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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