Diisopropylethylamine → HCID 68403216, compound

HRID 1029161Notes

Reaction equation

HRID 1029161 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:22]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=1)=[C:23]=[O:24].CCN(C(C)C)C(C)C>O1CCOCC1>[CH:31]([C:28]1[CH:29]=[CH:30][C:25]([NH:22][C:23]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:16]=[CH:15][N:14]=[C:13]4[C:8]=3[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[C:11](=[O:17])[NH:12]4)[CH2:6][CH2:5]2)=[O:24])=[CH:26][CH:27]=1)([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94416p-Isopropylphenyl isocyanateHCID 69815544HCID 69815544, compound

Product 1

HCID 68403216HCID 68403216, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Compound 179 (50 mg, 0.14 mmol), 1-isocyanato-4-isopropyl-benzene (34 mg, 0.21 mmol), and DIEA (0.07 mL, 0.42 mmol) were suspended in dioxane (2 mL), and stirred overnight at 80° C. The reaction mixture was quenched with 1M HCl, and diluted with EtOAc. The mixture was filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 75 to 100 EtOAc in hexane to provide 197 (40 mg, 64% yield) as a yellow solid. LC-MS (M+H=442, obsd.=442).

Workup

  1. customThe reaction mixture was quenched with 1M HCl
  2. additiondiluted with EtOAc
  3. filtrationThe mixture was filtered through an Extrelut column
  4. washThe column was washed with EtOAc
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified via Biotage
  7. washeluting with a gradient of 75 to 100 EtOAc in hexane

Sources & evidence

ORD record
ord-c9721f5b03054beeabc177c30372fbea
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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