Phthalimide → HCID 90052182, compound

HRID 2284808Notes

Reaction equation

HRID 2284808 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:24][CH2:25][CH3:26])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([C:27]#[C:28][CH2:29][CH2:30][CH2:31]O)=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2].[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:24][CH2:25][CH3:26])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:13]([C:27]#[C:28][CH2:29][CH2:30][CH2:31][N:37]3[C:33](=[O:43])[C:34]4[C:35](=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:36]3=[O:38])=[CH:12][N:11]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

9

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 90052195HCID 90052195, compound

Product 1

HCID 90052182HCID 90052182, compoundYield 90.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (2-((4-cyanophenyl)amino)-5-(5-hydroxy-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate (S11, 17 mg), phthalimide (12 mg) and triphenylphosphine (21 mg) in tetrahydrofuran (1 mL), a 2.2 mol/mL solution of diethyl azodicarboxylate in toluene (36 μL) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent, 100 to 40% hexane in ethyl acetate) to obtain tert-butyl (2-((4-cyanophenyl)amino)-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate (S12, 20 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (eluent, 100 to 40% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-6cca24d5c06a4abd89f15d45101250b9
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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