Trifluoroacetic acid → Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

HRID 1432951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432951
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:24])[C:18]=2[CH:17]=[C:16]1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:28][C:27]1=[O:42])=O)(C)(C)C>C(Cl)Cl>[CH2:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:16]2[NH:15][C:23]3[CH:22]=[CH:21][N:20]=[C:19]([Cl:24])[C:18]=3[CH:17]=2)[C:27](=[O:42])[CH2:28]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86760978HCID 86760978, Verbindung

Produkt 1

HCID 53757606Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Trifluoroacetic acid (10 mL) is added to a solution of 2-(4-benzyloxycarbonyl-2-oxo-piperazin-1-ylmethyl)-4-chloro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (5.66 g, 11.3 mmol, prepared in the same manner as described previously) in CH2Cl2 (10 mL). The solution is stirred overnight then diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (3.81 g, 9.56 mmol) as a foamy yellow solid. 1H NMR (CDCl3, 300 MHz) δ9.43 (bs, 1H), 8.08 (d, 1H), 7.38 (s, 5H), 7.18 (d, 1H), 6.51 (s, 1H), 5.15 (s, 2H), 4.58 (s, 2H), 4.20 (s, 2H), 3.71 (m, 2H), 3.50 (m, 2H). Ion spray [M+H]+=399, 401, Cl pattern.

Aufarbeitung

  1. customprepared in the same manner
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product is chromatographed
  7. washeluting with 1-5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-89c763872df94fb49082851a202ac181
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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