3-Amino-9-ethylcarbazole → HCID 86729749, compound

HRID 2272590Notes

Reaction equation

HRID 2272590 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=O)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[N:25]([CH2:34][CH3:35])[C:26]3[C:31]([C:32]=2[CH:33]=1)=[CH:30][CH:29]=[CH:28][CH:27]=3.[CH3:36][CH2:37]N(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]([CH2:36][CH3:37])[CH2:10][CH2:11][CH2:12][C:13]([NH:20][C:21]2[CH:22]=[CH:23][C:24]3[N:25]([CH2:34][CH3:35])[C:26]4[C:31]([C:32]=3[CH:33]=2)=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:15])=[O:8])=[CH:18][CH:19]=1)#[N:2]

Participants

7

Reactant 4

HCID 85883-Amino-9-ethylcarbazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60637584HCID 60637584, compound

Product 1

HCID 86729749HCID 86729749, compoundYield 11.56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Step 1 (0.23 g, 0.76 mmol), 3-amino-N-ethylcarbazole (159 mg, 0.76 mmol) and DIEA (0.396 mL, 2.27 mmol) in DMF (6 mL) was added HATU (359 mg, 0.94 mmol), and the mixture was stirred at room temperature for 14 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. 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; 10 to 100% ethyl acetate/hexane) to give the title compound (43.4 mg, 0.087 mmol, 11.56%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  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; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-307ba9f364404d7db7d488b8529f40d8
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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