Pyridine → Methyl 2-(4-(propylcarbamoyl)phenylcarbamoyl)isoindoline-5-carboxylate

HRID 624112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624112
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH3:11])=[O:7])=[CH:4][CH:3]=1.[C:14](=O)(ON1C(=O)CCC1=O)[O:15]N1C(=O)CCC1=O.N1C=CC=CC=1.C(N(C(C)C)CC)(C)C.Cl.[CH2:48]1[C:56]2[C:51](=[CH:52][C:53]([C:57]([O:59][CH3:60])=[O:58])=[CH:54][CH:55]=2)[CH2:50][NH:49]1>C(#N)C.CN1CCCC1=O.O>[CH2:9]([NH:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:14]([N:49]2[CH2:50][C:51]3[C:56](=[CH:55][CH:54]=[C:53]([C:57]([O:59][CH3:60])=[O:58])[CH:52]=3)[CH2:48]2)=[O:15])=[CH:13][CH:12]=1)=[O:7])[CH2:10][CH3:11]

Komponenten

9

Edukt 5

HCID 1049PyridineHCID 81531Diisopropylethylamine2×HCID 4283444-amino-N-propylbenzamideHCID 676246Di(succinimido) carbonateHCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride

Produkt 1

HCID 57509896Methyl 2-(4-(propylcarbamoyl)phenylcarbamoyl)isoindoline-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 4-amino-N-propylbenzamide (390 mg, 2.19 mmol), bis(2,5-dioxopyrrolidin-1-yl) carbonate (700 mg, 2.74 mmol), and pyridine (0.18 mL, 2.19 mmol) in acetonitrile (5 mL) was stirred at ambient temperature for 30 minutes. Diisopropylethylamine (0.85 mL, 6.6 mmol)) was added followed by a suspension of methyl isoindoline-5-carboxylate hydrochloride (538 mg, 2.52 mmol) and diisopropylethylamine (0.46 mL, 4.4 mmol) in 1-methyl-2-pyrrolidinone (8 mL) added dropwise via syringe over ˜5 minutes. The reaction became a suspension and was stirred 3 hours. The reaction was treated with water (30 mL) and the resulting suspension was stirred 5 minutes and filtered. The solid collected was washed with water and dried under vacuum to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.63 (s, 1H), 8.26 (t, J=5.6 Hz, 1H), 7.94-7.97 (m, 1H), 7.90-7.96 (m, 1H), 7.75-7.78 (m, 2H), 7.63-7.67 (m, 2H), 7.52 (d, J=7.9 Hz, 1H), 4.83-4.86 (m, 4H), 3.87 (s, 3H), 3.16-3.22 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 382 (M+H)+.

Aufarbeitung

  1. additionadded dropwise via syringe over ˜5 minutes
  2. stirringthe resulting suspension was stirred 5 minutes
  3. filtrationfiltered
  4. customThe solid collected
  5. washwas washed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b9cf5fa28fe247d69dd1e813c90c7acf
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302989B2

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