3-Amino-9-ethylcarbazole → HCID 86729718, compound

HRID 2272554Notes

Reaction equation

HRID 2272554 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:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:34])[CH2:27][CH:28]([CH3:33])[CH2:29][C:30](O)=[O:31])#[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:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:34])[CH2:27][CH:28]([CH3:33])[CH2:29][C:30]([NH:16][C:12]1[CH:13]=[CH:14][C:15]2[N:3]([CH2:1][CH3:2])[C:4]3[C:9]([C:10]=2[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:31])#[N:18]

Participants

8

Reactant 5

HCID 85883-Amino-9-ethylcarbazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 55155791HCID 55155791, compound

Product 1

HCID 86729718HCID 86729718, compoundYield 40.4%

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 (239 mg, 0.97 mmol), HOBt (297 mg, 1.94 mmol) and WSC (372 mg, 1.94 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 precipitate was collected by filtration, and recrystallized from methanol and THF to give the title compound (172 mg, 0.392 mmol, 40.4%) as a white powder.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customrecrystallized from methanol and THF

Sources & evidence

ORD record
ord-3c34001f74ee4e9e9f9b34caed5c5bbf
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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