3-Amino-9-ethylcarbazole → HCID 86729774, compound

HRID 2272617Notes

Reaction equation

HRID 2272617 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=O)=[CH:5][C:4]=1[O:19][CH3:20])#[N:2].[CH2:21]([N:23]1[C:35]2[CH:34]=[CH:33][C:32]([NH2:36])=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22].CCN(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:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([NH:36][C:32]2[CH:33]=[CH:34][C:35]3[N:23]([CH2:21][CH3:22])[C:24]4[C:29]([C:30]=3[CH:31]=2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:16])=[CH:5][C:4]=1[O:19][CH3:20])#[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 86729773HCID 86729773, compound

Product 1

HCID 86729774HCID 86729774, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Step 2 (1.20 g, 4.34 mmol), 9-ethyl-9H-carbazol-3-amine (0.913 g, 4.34 mmol) and DIEA (1.896 mL, 10.86 mmol) in DMF (15 mL) was added HATU (1.982 g, 5.21 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added water, 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 85% ethyl acetate/hexane), and purified by NH-silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give the title compound (0.788 g, 1.681 mmol, 38.7%) as a colorless 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 85% ethyl acetate/hexane)
  6. custompurified by NH-silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6aa9e09706694c8dbd12cd28eda54ae4
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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