Propylamine → 4-methyl-N-propyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 222976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222976
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.CN(C(O[N:28]1N=N[C:30]2[CH:31]=CC=C[C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(N)CC>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:28][CH2:29][CH2:30][CH3:31])=[O:7])=[CH:4][C:3]=1[B:11]1[O:12][C:13]([CH3:19])([CH3:18])[C:14]([CH3:17])([CH3:16])[O:15]1

Komponenten

6

Edukt 4

HCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Produkt 1

HCID 574345484-methyl-N-propyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (524 mg, 2 mmol, 1 eq) was added HBTU (642 mg, 2 mmol, 1 eq) in DMF (5 mL). DIPEA (700 uL, 4 mmol, 2 eq) was then added in 100 uL portions. After 10 min propylamine (328 uL, 4 mmol, 2 eq) was then added and the mixture was stirred overnight at room temperature. The solvent was then removed in vacuo. The residue was then dissolved in chloroform and purified by aminopropyl SPE: LC-MS m/z 304 (M+H)+, 3.37 min (ret time).

Aufarbeitung

  1. customThe solvent was then removed in vacuo
  2. dissolutionThe residue was then dissolved in chloroform
  3. custompurified by aminopropyl SPE
  4. customLC-MS m/z 304 (M+H)+, 3.37 min (ret time)

Quellen und Nachweise

ORD-Eintrag
ord-55e550e173834cb894c34b4003eb7554
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207176B2

Notizen zur Reaktion

Wird geladen…