3-Amino-9-ethylcarbazole → N-(4-cyanophenyl)-5-[(9-ethyl-9H-carbazol-3-yl)amino]-3-methylpentanamide

HRID 2272561Notes

Reaction equation

HRID 2272561 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])[CH2:11][CH:12]([CH3:16])[CH2:13][CH:14]=O)=[CH:5][CH:4]=1)#[N:2].[NH2:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([CH2:32][CH3:33])[C:24]3[C:29]([C:30]=2[CH:31]=1)=[CH:28][CH:27]=[CH:26][CH:25]=3.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])[CH2:11][CH:12]([CH3:16])[CH2:13][CH2:14][NH:18][C:19]2[CH:20]=[CH:21][C:22]3[N:23]([CH2:32][CH3:33])[C:24]4[C:29]([C:30]=3[CH:31]=2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 5049666Sodium triacetoxyborohydrideHCID 86729722N-(4-cyanophenyl)-3-methyl-5-oxopentanamide

Product 1

HCID 86729723N-(4-cyanophenyl)-5-[(9-ethyl-9H-carbazol-3-yl)amino]-3-methylpentanamideYield 40.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the compound obtained in Step 2 (110 mg, 0.48 mmol) and 3-amino-N-ethylcarbazole (151 mg, 0.72 mmol) in TFA (1 mL) and toluene (1 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added sodium triacetoxyborohydride (304 mg, 1.43 mmol), and the mixture was stirred at room temperature for additional 14 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with 1N aqueous sodium hydroxide solution, water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 80% ethyl acetate/hexane) to give the title compound (82 mg, 0.193 mmol, 40.5%) as a pale-yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1N aqueous sodium hydroxide solution, water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-53eecf6a4eb34ad48819c0ec56335949
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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