9-Ethyl-2,3,4,9-tetrahydro-1h-carbazol-6-amine → HCID 71508397, compound

HRID 2272558Notes

Reaction equation

HRID 2272558 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][CH:4]=1)#[N:2].[CH2:19]([N:21]1[C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[C:25]([NH2:34])[CH:26]=2)[CH3:20].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>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([NH:34][C:25]2[CH:26]=[C:27]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:19][CH3:20])[C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]3=2)=[O:16])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 446179-Ethyl-2,3,4,9-tetrahydro-1h-carbazol-6-amineHCID 81531DiisopropylethylamineHCID 3981627HCID 3981627, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71508397HCID 71508397, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (172 mg, 0.70 mmol), 9-ethyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine (150 mg, 0.70 mmol) and DIEA (0.367 mL, 2.10 mmol) in DMF (8 mL) was added HATU (399 mg, 1.05 mmol), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was separated, 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) to give the title compound (179 mg, 0.404 mmol, 57.8%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-abc078bc4f524bb0a99da014d7c9504c
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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