3-Amino-9-ethylcarbazole → HCID 86729731, compound

HRID 2272572Notes

Reaction equation

HRID 2272572 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[C:19]([F:22])([F:21])[F:20])#[N:2].[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([CH2:37][CH3:38])[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3.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.C(OCC)(=O)C.CCCCCC.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:23][C:24]2[CH:25]=[CH:26][C:27]3[N:28]([CH2:37][CH3:38])[C:29]4[C:34]([C:35]=3[CH:36]=2)=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:16])=[CH:5][C:4]=1[C:19]([F:22])([F:21])[F:20])#[N:2]

Participants

8

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 86729730HCID 86729730, compound

Product 1

HCID 86729731HCID 86729731, compoundYield 39.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of the compound obtained in Step 1 (300 mg, 0.95 mmol), 3-amino-9-ethylcarbazole (241 mg, 1.15 mmol) and DIEA (0.500 mL, 2.86 mmol) in DMF (6 mL) was added HATU (544 mg, 1.43 mmol), and the mixture was stirred at room temperature for 14 hr. To the reaction solution 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; 5 to 75% ethyl acetate/hexane), and then NH-silica gel column chromatography (solvent gradient; 5 to 100% ethyl acetate/hexane) to give the title compound (189 mg, 0.372 mmol, 39.0%) 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; 5 to 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-95aedc1efbf2498287d6a21b2b828a2f
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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