3-Amino-9-ethylcarbazole → HCID 86729772, compound

HRID 2272614Notes

Reaction equation

HRID 2272614 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([CH:13]2[CH2:16][CH2:15][CH:14]2[C:17]([OH:19])=O)=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH2:20]([N:22]1[C:34]2[CH:33]=[CH:32][C:31]([NH2:35])=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([CH:13]2[CH2:16][CH2:15][CH:14]2[C:17]([NH:35][C:31]2[CH:32]=[CH:33][C:34]3[N:22]([CH2:20][CH3:21])[C:23]4[C:28]([C:29]=3[CH:30]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:19])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729771HCID 86729771, compound

Product 1

HCID 86729772HCID 86729772, compoundYield 6.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of the compound obtained in Step 1 (795 mg, 2.85 mmol), 9-ethyl-9H-carbazol-3-amine (600 mg, 2.85 mmol), HATU (1085 mg, 2.85 mmol) and TEA (0.437 mL, 3.14 mmol) in DMF (5 mL) was stirred at room temperature for 14 hr. To the reaction mixture was added brine at room temperature, 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), and crystallized from ethyl acetate and ethanol to give the title compound (82 mg, 0.174 mmol, 6.10%) as colorless crystals.

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)
  6. customcrystallized from ethyl acetate and ethanol

Sources & evidence

ORD record
ord-0ed3f8025a714a5185cb6e94013cc451
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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