Triethylamine → HCID 90051807, compound

HRID 2284804Notes

Reaction equation

HRID 2284804 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[N:16][OH:17])=[CH:13][N:12]=[C:11]([S:18][CH3:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)CCC1=O.[CH2:28]([N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42])[CH2:29][C:30]#[CH:31].C(N(CC)CC)C>CN(C)C=O.N1C=CC=CC=1.O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:31]=[C:30]([CH2:29][CH2:28][N:32]3[C:36](=[O:37])[C:35]4[C:34](=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:33]3=[O:42])[O:17][N:16]=2)=[CH:13][N:12]=[C:11]([S:18][CH3:19])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 11171619N-(3-Butynyl)phthalimideHCID 90051806HCID 90051806, compound

Product 1

HCID 90051807HCID 90051807, compoundYield 36.3%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carbaldehyde oxime (S21, 705 mg) in N,N-dimethylformamide (6.0 mL), pyridine (20.6 μL) and N-chlorosuccinimide (471 mg) were added under ice cooling, and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, then a solution of N-(3-butynyl)phthalimide (765 mg) and triethylamine (603 μL) in tetrahydrofuran (8.5 mL) was added to the reaction mixture, and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed successively with water and 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 column chromatography to obtain 2-(2-(3-(4-(benzyloxy)-2-(methylthio)pyrimidin-5-yl)isoxazol-5-yl)ethyl)isoindoline-1,3-dione (S22, 439 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at 50° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washwashed successively with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-92bd97ec082f4796bca5700830f65fbc
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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