3-Amino-9-ethylcarbazole → HCID 86729770, compound

HRID 2272612Notes

Reaction equation

HRID 2272612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:24])[CH2:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH2:25]([N:27]1[C:39]2[CH:38]=[CH:37][C:36]([NH2:40])=[CH:35][C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH3:26].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](=[O:24])[CH2:12][CH:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][C:15]([NH:40][C:36]2[CH:37]=[CH:38][C:39]3[N:27]([CH2:25][CH3:26])[C:28]4[C:33]([C:34]=3[CH:35]=2)=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:17])[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 86729768HCID 86729768, compound

Product 1

HCID 86729770HCID 86729770, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of the compound obtained in Step 1 (1.2 g, 3.50 mmol), 9-ethyl-9H-carbazol-3-ylamine (0.736 g, 3.50 mmol), HATU (1.464 g, 3.85 mmol) and TEA (0.537 mL, 3.85 mmol) in DMF (10 mL) was stirred at room temperature for 3 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 50% ethyl acetate/hexane), and crystallized from ethyl acetate to give the title compound (0.187 g, 0.350 mmol, 9.98%) as white 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 50% ethyl acetate/hexane)
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ba228f955d1a4b31ba9cb3e63e9a8ca2
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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