3-Amino-9-ethylcarbazole → HCID 86729719, compound

HRID 2272555Notes

Reaction equation

HRID 2272555 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[C:17]([C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:34])[CH2:27][CH:28]([CH3:33])[CH2:29][C:30](O)=[O:31])[CH:22]=[CH:23][CH:24]=1)#[N:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:17]([C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:34])[CH2:27][CH:28]([CH3:33])[CH2:29][C:30]([NH:16][C:12]2[CH:13]=[CH:14][C:15]3[N:3]([CH2:1][CH3:2])[C:4]4[C:9]([C:10]=3[CH:11]=2)=[CH:8][CH:7]=[CH:6][CH:5]=4)=[O:31])[CH:22]=[CH:23][CH:24]=1)#[N:18]

Participants

8

Reactant 5

HCID 85883-Amino-9-ethylcarbazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 2732326HCID 2732326, compound

Product 1

HCID 86729719HCID 86729719, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9-ethyl-9H-carbazol-3-amine (210 mg, 1.00 mmol), the compound obtained in Step 1 (246 mg, 1 mmol), HOBt (306 mg, 2.00 mmol) and WSC (383 mg, 2.00 mmol) in DMF (5 mL) was stirred at room temperature for 14 hr. The reaction mixture was poured into a mixed solution of aqueous sodium hydrogen carbonate solution and ethyl acetate, and the organic layer was separated. The organic layer was washed with 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; 66 to 80% ethyl acetate/hexane) to give the title compound (283 mg, 0.645 mmol, 64.5%) as a white powder.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 66 to 80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8feec6e4de1d4470b52c916c079eaa44
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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