9-Ethyl-9H-carbazole-3-carboxylic acid → HCID 71538151, compound

HRID 2272623Notes

Reaction equation

HRID 2272623 reaction equation
[NH2:1][CH2:2][CH:3]([CH3:17])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([Cl:16])[CH:9]=1)=[O:6].[CH2:18]([N:20]1[C:32]2[CH:31]=[CH:30][C:29]([C:33](O)=[O:34])=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19].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:16][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][CH:3]([CH3:17])[CH2:2][NH:1][C:33]([C:29]2[CH:30]=[CH:31][C:32]3[N:20]([CH2:18][CH3:19])[C:21]4[C:26]([C:27]=3[CH:28]=2)=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:34])[CH:13]=[CH:12][C:11]=1[C:14]#[N:15]

Participants

6

Reactant 3

HCID 49128699-Ethyl-9H-carbazole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 81071596HCID 81071596, compound

Product 1

HCID 71538151HCID 71538151, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of the compound obtained in Step 3 (158 mg, 0.63 mmol), 9-ethyl-9H-carbazole-3-carboxylic acid (150 mg, 0.63 mmol), HATU (262 mg, 0.69 mmol) and TEA (0.096 mL, 0.69 mmol) in DMF (5 mL) was stirred at 50° C. for 14 hr. To the reaction solution 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 80% ethyl acetate/hexane) to give the title compound (156 mg, 0.330 mmol, 52.6%) 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 80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a06c08c40e7a417cb2c2cdf6d789d96a
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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