Diisopropylethylamine → HCID 66589936, compound

HRID 1092368Notes

Reaction equation

HRID 1092368 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15](=[O:42])[N:16]([CH:18]1[CH2:23][CH2:22][CH:21]([NH:24][CH2:25][C:26]2[CH:27]=[C:28]([C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)[C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH2:20][CH2:19]1)[CH3:17])([CH3:13])([CH3:12])[CH3:11].[Cl:43][C:44]1[C:45]2[CH:55]=[CH:54][CH:53]=[CH:52][C:46]=2[S:47][C:48]=1[C:49](Cl)=[O:50]>ClCCl>[C:10]([O:14][C:15](=[O:42])[N:16]([CH:18]1[CH2:23][CH2:22][CH:21]([N:24]([C:49]([C:48]2[S:47][C:46]3[CH:52]=[CH:53][CH:54]=[CH:55][C:45]=3[C:44]=2[Cl:43])=[O:50])[CH2:25][C:26]2[CH:27]=[C:28]([C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)[C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH2:20][CH2:19]1)[CH3:17])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 66590460HCID 66590460, compound

Product 1

HCID 66589936HCID 66589936, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (2.1 mL, 12.1 mmol) was added to a solution of amine 5 (2.2 g, 4.9 mmol), 3-chlorobenzo[b]thiophene-2-carbonyl chloride (1.3 g, 5.86 mmol) and anhydrous dichloromethane (22 mL), with stirring under argon. Once all of the starting material had been consumed as monitored by TLC (˜2.5 hours), the mixture was washed with water, saturated aqueous sodium hydrogen carbonate, and brine. The organic layer was dried (MgSO4), and concentrated in vacuo. The yellow residue was then purified by silica-gel chromatography using hexane/ethyl acetate 3:1 to give the title compound 6 (2.93 g, 93%) as a pale yellow solid.

Workup

  1. customOnce all of the starting material had been consumed
  2. customas monitored by TLC (˜2.5 hours)
  3. washthe mixture was washed with water, saturated aqueous sodium hydrogen carbonate, and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe yellow residue was then purified by silica-gel chromatography

Sources & evidence

ORD record
ord-9c7464070c094cfa9617e6496667fbf2
Source dataset
uspto-grants-2012_03
Patent number
US08129425B2

Reaction notes

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