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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 1501848
Notes
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Reaction equation

HRID 1501848 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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 (1 H. , d, J=7.8 Hz), 5.34 (2 H, s), 5.32 (2 H, s), 5.26 (2 H, s), 4.03 (2 H, t, J=7.0 Hz), 3.71 (1 H, m), 3.15 (1 H, m), 2.94 (2 H, m), 2.47 (2 H, t, J=7.0 Hz), 2.42 (3 H, s), 2.17 (2 H, m), 2.07 (3 H, s), 2.02 (2 H, m), 1.58 (2 H, 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-c61cc76135c64a23afe4b96dd6b6503a
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206198B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes