Triethylamine → 1-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]ethane-1,2-dione

HRID 1157755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157755
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([F:16])=[C:6]2[C:10]([C:11](=[O:15])[C:12]([OH:14])=O)=[CH:9][NH:8][C:7]=12.[C:17]1([N:23]2[C:27]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:26][N:25]=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CN(C1C=CN=CC=1)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([F:16])=[C:6]2[C:10]([C:11](=[O:15])[C:12]([N:31]3[CH2:32][CH2:33][N:28]([C:27]4[N:23]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[N:24]=[N:25][N:26]=4)[CH2:29][CH2:30]3)=[O:14])=[CH:9][NH:8][C:7]=12

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 38255781-(1-Phenyl-1H-tetrazol-5-YL)piperazineHCID 595111932-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

Produkt 1

HCID 248752521-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]ethane-1,2-dioneAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (2.3 g, 10.0 mmol) was dissolved in DMF (66 mL) and treated with 1-(1-phenyl-1H-tetrazol-5-yl)piperazine (2.31 g, 10.0 mmol), triethylamine (2.8 mL, 20.0 mmol) and TBTU (3.5 g, 11.0 mmol) and a catalytic amount of DMAP. The reaction mixture was stirred at rt for 18 h. Solvent was removed in vacuum and water was added. A white solid precipitated out and it was collected by filtration and recrystallized with MeOH to afford the title compound (2.4 g) as a yellow solid. 1HNMR (500 MHz, DMSO-D6) δ 8.53 (s, 1H), 7.81 (d, J=4.0 Hz; 1H), 7.75-7.54 (m, 5H), 3.69 (m, 2H), 3.44 (m, 2H), 3.33 (m, 2H), 3.17 (m, 2H). LCMS: m/e 436 (M+H)+, ret time 1.73 min (method 2).

Aufarbeitung

  1. customSolvent was removed in vacuum and water
  2. additionwas added
  3. customA white solid precipitated out
  4. filtrationit was collected by filtration
  5. customrecrystallized with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-d2392415ac4e414d87e8ad8e4465f3da
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807676B2

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