Diisopropylethylamine → N-(4-cyanophenyl)-3-methyl-N'-(9-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-yl)pentanediamide

HRID 2272575Notes

Reaction equation

HRID 2272575 reaction equation
[CH2:1]([N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([NH2:17])[CH:9]=2)[CH2:2][CH3:3].[C:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[CH2:28][CH:29]([CH3:34])[CH2:30][C:31](O)=[O:32])=[CH:22][CH:21]=1)#[N:19].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:18]([C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:35])[CH2:28][CH:29]([CH3:34])[CH2:30][C:31]([NH:17][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([CH2:1][CH2:2][CH3:3])[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]3=2)=[O:32])=[CH:24][CH:25]=1)#[N:19]

Participants

7

Reactant 4

HCID 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)HCID 867297339-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine

Product 1

HCID 86729734N-(4-cyanophenyl)-3-methyl-N'-(9-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-yl)pentanediamideYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Step 2 (229 mg, 1.00 mmol), 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (247 mg, 1.00 mmol) and DIEA (0.525 mL, 3.01 mmol) in DMF (6 mL) was added HATU (572 mg, 1.50 mmol), and the mixture was stirred at room temperature for 14 hr. 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; 5 to 75% ethyl acetate/hexane) to give the title compound (151 mg, 0.332 mmol, 33.1%) as a white 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; 5 to 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-88db441f9c7c4cc795422f9a25625605
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

Loading…