Water → HCID 11590985, compound

HRID 1677835Notes

Reaction equation

HRID 1677835 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18]([N:22]([CH2:31][CH2:32][CH2:33][N:34]1C(=O)C2C(=CC=CC=2)C1=O)[C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O>CCO>[NH2:34][CH2:33][CH2:32][CH2:31][N:22]([CH:18]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:19]([CH3:21])[CH3:20])[C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 57894427HCID 57894427, compound

Product 1

HCID 11590985HCID 11590985, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of product of step 10 (50 mg) in 1 mL of EtOH was added hydrazine (0.1 mL). The mixture was stirred at room temperature for 2 h. The solution was poured into water, and extracted with EtOAc (×3). The organic layers were combined, washed with 10% NaOH aq., H2O (×3), brine (×3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified preparatory HPLC to give N-(3-aminopropyl)-N-[1-(1-benzyl-5-chloro-1H-indol-2-yl)-2-methylpropyl]benzamide.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with 10% NaOH aq., H2O (×3), brine (×3)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe material was purified preparatory HPLC

Sources & evidence

ORD record
ord-22341461c63c4988a25359f48432b086
Source dataset
uspto-grants-2011_08
Patent number
US08008335B2

Reaction notes

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