Diisopropylethylamine → 8-(2-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848538Notes

Reaction equation

HRID 1848538 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH2:4][C:3]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]1=[O:18].Br[CH2:20][C:21]([C:23]1[C:24]([CH3:33])=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[O:27][CH2:26]2)=[O:22].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:33][C:24]1[C:23]([C:21](=[O:22])[CH2:20][N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:18])[N:8]([C:3]4[CH2:4][O:5][C:6](=[O:7])[C:2]=4[CH3:1])[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][O:27][C:28]2=[O:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 772312635-(2-bromoacetyl)-4-methylisobenzofuran-1(3H)-oneHCID 867095242-(4-Methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 867095278-(2-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-17) (2 g, 7.99 mmol), 5-(2-Bromo-acetyl)-4-methyl-3H-isobenzofuran-1-one (I-4B, method 2, step F) (2.150 g, 7.99 mmol) and N-ethyl-N-isopropylpropan-2-amine (3.48 mL, 19.98 mmol) in DCM (50 mL) were stirred overnight at rt. The mixture was washed with saturated ammonium chloride aqueous and brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was used in the next step without further purification. 1H-NMR (500 MHz, CDCl3): δ ppm 7.83 (1H, d, J=7.8 Hz), 7.79 (1H. d, J=7.8 Hz), 5.34 (2H, s), 5.32 (2H, s), 5.26 (2H, s), 4.03 (2H, t, J=7.0 Hz), 3.71 (1H, m), 3.15 (1H, m), 2.94 (2H, m), 2.47 (2H, t, J=7.0 Hz), 2.42 (3H, s), 2.17 (2H, m), 2.07 (3H, s), 2.02 (2H, m), 1.58 (2H, m). LCMS 438.9 (M+1).

Workup

  1. washThe mixture was washed with saturated ammonium chloride aqueous and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-6a0fc7c6b49741f482580aef5358f33a
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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