Diisopropylethylamine → HCID 86659915, compound

HRID 2360189Notes

Reaction equation

HRID 2360189 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[C:12]([CH3:21])([CH3:20])[CH2:11]1.Cl[C:23]([O:25][C:26]1C=C[C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=1)=O.C(N(C(C)C)CC)(C)C.[O:44]1CCC(CN)[CH2:45]1>O1CCCC1.O>[O:25]1[CH2:26][CH2:27][CH:28]([CH2:29][NH:32][C:45](=[O:44])[O:19][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:10]([CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)[CH2:11][C:12]3([CH3:21])[CH3:20])[CH2:23]1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 10898660(Tetrahydrofuran-3-yl)methanamineHCID 86659916HCID 86659916, compound

Product 1

HCID 86659915HCID 86659915, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(2-pyridylmethyl)-3,3-dimethylindolin-5-ol dihydrochloride (50.0 mg, 0.15 mmol) in 1 mL of dry tetrahydrofuran was added 4-nitrophenyl chloroformate (34 mg, 0.165 mmol) and diisopropylethylamine (91 μL, 0.52 mmol) under ice-cooled conditions. After the reaction mixture was stirred at room temperature for 1 h, 3-tetrahydrofurylmethylamine (17 μL, 0.165 mmol) and diisopropylethylamine (39 μL, 0.225 mmol) was added with additional stirring overnight. After the reaction mixture was added with water (10 mL), the solution was extracted with ethyl acetate (10 mL). The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 10/90) to obtain the title compound (10.7 mg, 18%) as a white solid having the following characteristics.

Workup

  1. temperaturecooled conditions
  2. stirringwith additional stirring overnight
  3. extractionthe solution was extracted with ethyl acetate (10 mL)
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 10/90)

Sources & evidence

ORD record
ord-afdc6271aac04dc4953096022db70b43
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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