Propylamine → N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide

HRID 1581993Notes

Reaction equation

HRID 1581993 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=O)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][CH3:23].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:21]([NH:24][C:18]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17]2)=[O:20])[CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 227195982-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylic acid

Product 1

HCID 22719592N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamideYield 63.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(tert-butoxycarbonylamino)-5-carboxyindan (30 mg, 0.11 mmol) synthesized in Preparation Example 4, n-propylamine (20 μl, 0.24 mmol), triethylamine (0.20 ml, 1.4 mmol), propanephosphonic acid anhydride (0;3 ml) (see Japanese Unexamined Patent Publication (Kokai) No. 55-100346), and dimethylaminopyridine (a catalytic amount) in methylene chloride (0.25 ml) were stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and then washed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine, an aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 3:7) to obtain N-propyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide (22 mg, 0.070 mmol) having the following-physical properties:

Workup

  1. washwashed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine
  2. dry with materialan aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 3:7)

Sources & evidence

ORD record
ord-7b58f28862594ab2a1d6a1cbeef7b57d
Source dataset
uspto-grants-2004_05
Patent number
US06734180B1

Reaction notes

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