Diisopropylethylamine → HCID 58880139, compound

HRID 1642527Notes

Reaction equation

HRID 1642527 reaction equation
ClC1N=[C:4]([NH:18][C:19]2[C:24]([C:25]#[C:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][C:22]([Cl:31])=[CH:21][N:20]=2)[C:5](=[O:17])[N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:7]=1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:31][C:22]1[CH:21]=[N:20][C:19]2[NH:18][C:4]3[C:5](=[O:17])[N:6]([CH2:8][C:9]4[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=4)[CH:7]=[C:26]([Si:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=3[C:24]=2[CH:23]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 58880164HCID 58880164, compound

Product 1

HCID 58880139HCID 58880139, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 66 (5.8 g, 12.3 mmol) and DIEA (3.2 mL, 18.4 mmol) were dissolved in toluene (600 mL), and the solution was heated at reflux under N2 for four days. The solution was concentrated and purified by flash chromatography (30% EtOAc/CH2Cl2) to give 4.4 g (87%) of the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 12.98 (s, 1H), 8.54 (d, 1H, J=2.4 Hz), 8.20 (d, 1H, J=2.4 Hz), 7.37 (s, 1H), 7.32 (d, 2H, J=8.8 Hz), 6.90 (d, 2H, J=8.8 Hz), 5.25 (s, 2H), 3.71 (s, 3H), 0.39 (s, 9H). MS (ES) [m+H] calc'd for C21H22ClN3O2Si, 412, 414; found 412, 414.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux under N2 for four days
  3. concentrationThe solution was concentrated
  4. custompurified by flash chromatography (30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-f8ae4303c5984d46bb21d6d80ffeeb21
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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