Benzylamine → 6-benzyl-4-(3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

HRID 41882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41882
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[CH2:19][O:20][C:21](=[O:22])[C:14]=34)=[CH:11][N:10]([CH3:23])[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(=O)C>[CH2:24]([N:31]1[C:21](=[O:22])[C:14]2[C:15](=[N:16][CH:17]=[CH:18][C:13]=2[C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][N:10]([CH3:23])[CH:11]=2)[C:19]1=[O:20])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 679718214-[3-(4-Fluorophenyl)-1-methyl-1H-pyrazol-4-yl]furo[3,4-b]pyridin-5(7H)-one

Produkt 1

HCID 679717066-benzyl-4-(3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-[3-(4-Fluorophenyl)-1-methyl-1H-pyrazol-4-yl]furo[3,4-b]pyridin-5(7H)-one (Example 1, step 5, 472 mg, 1.46 mmol) and benzyl amine (0.167 mL, 1.53 mmol) in acetic acid (4.7 mL) were heated at reflux for 18 hr, cooled and then concentrated to a brown solid. This material was stirred with diethyl ether (20 mL) for 10 min and then filtered to yield 450 mg (75%) of Ex 5-Step 1 product as a tan colored solid: LCMS m/z 413.5 (M+1); 1H NMR (400 MHz, CDCl3) δ 8.57 (d, J=5.2, 1H), 8.15 (s, 1H), 7.26-7.42 (m, 7H), 7.13 (d, J=5.3, 1H), 7.01 (dd, J=8.6, 8.6, 2H), 4.87 (s, 2H), 4.00 (s, 3H).

Aufarbeitung

  1. temperatureat reflux for 18 hr
  2. temperaturecooled
  3. concentrationconcentrated to a brown solid
  4. filtrationfiltered
  5. customto yield 450 mg (75%) of Ex 5-Step 1 product as a tan colored solid

Quellen und Nachweise

ORD-Eintrag
ord-ce316869c633465c80d5bba21a1b3c64
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536164B2

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