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

HRID 2272578Notes

Reaction equation

HRID 2272578 reaction equation
[CH2:1]([N:5]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([NH2:18])[CH:10]=2)[CH:2]([CH3:4])[CH3:3].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:36])[CH2:29][CH:30]([CH3:35])[CH2:31][C:32](O)=[O:33])=[CH:23][CH:22]=1)#[N: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:19]([C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:28](=[O:36])[CH2:29][CH:30]([CH3:35])[CH2:31][C:32]([NH:18][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=2)=[O:33])=[CH:25][CH:26]=1)#[N:20]

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 867297369-isobutyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine

Product 1

HCID 86729737N-(4-cyanophenyl)-3-methyl-N'-[9-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-carbazol-6-yl]pentanediamideYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Step 2 (235 mg, 0.97 mmol), 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (239 mg, 0.97 mmol) and DIEA (0.508 mL, 2.91 mmol) in DMF (6 mL) was added HATU (553 mg, 1.45 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 (242 mg, 0.515 mmol, 53.1%) 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-ce24647ba16446d6857f46401542d9c7
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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