3-Amino-9-ethylcarbazole → HCID 86729738, compound

HRID 2272579Notes

Reaction equation

HRID 2272579 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])=[O:23])([CH3:20])([CH3:19])[CH3:18].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>[CH2:15]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][NH:24][C:22](=[O:23])[O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:16]

Participants

7

Reactant 4

HCID 85883-Amino-9-ethylcarbazoleHCID 81531DiisopropylethylamineHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86729738HCID 86729738, compoundYield 115%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-9-ethylcarbazole (500 mg, 2.38 mmol), 4-(tert-butoxycarbonylamino)butyric acid (483 mg, 2.38 mmol) and DIEA (1.246 mL, 7.13 mmol) in DMF (12 mL) was added HATU (1085 mg, 2.85 mmol), and the mixture was stirred at room temperature for 3 days. 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; 10 to 75% ethyl acetate/hexane) to give crude tert-butyl 4-(9-ethyl-9H-carbazol-3-ylamino)-4-oxobutylcarbamate (1080 mg, 2.73 mmol, 115%) as a pale-yellow 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 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d0a1fd99acdf4f7db3e8931cea4b551a
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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