Aniline → N-phenyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide

HRID 48429Notes

Reaction equation

HRID 48429 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](O)=[O:19])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:22]1([NH:21][C:18]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:17]3)=[O:19])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 227195982-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylic acid

Product 1

HCID 22719646N-phenyl-2-(tert-butoxycarbonylamino)-5-indan carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using 2-(tert-butoxycarbonylamino)-5-carboxyindan (30 mg, 0.11 mmol) synthesized in Reference Production Example 4, aniline (21 μl, 0.23 mmol), triethylamine (0.20 ml, 1.4 mmol), propanephosphonicacid anhydride (0.3 ml), dimethylaminopyridine (a catalytic amount) and methylene chloride (0.25 ml), a similar procedure to a) in Production Example 21 was carried out. The product obtained was purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 7:3) to obtain N-phenyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide (27 mg, 0.077 mmol) having the following physical properties:

Workup

  1. customThe product obtained
  2. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1 to 7:3)

Sources & evidence

ORD record
ord-eddf7110ca6c4dc599d6966e96ec6500
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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