Acetic Acid → HCID 178478340, Verbindung

HRID 1678789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678789
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)=[N:7]2.[NH:26]1[CH:30]=[N:29][C:28]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[N:27]1.C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:34]3[CH2:33][CH2:32][CH:31]([C:28]4[NH:29][CH:30]=[N:26][N:27]=4)[CH2:36][CH2:35]3)=[CH:14][CH:13]=1)=[N:7]2

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehydeHCID 178420874HCID 178420874, Verbindung

Produkt 1

HCID 178478340HCID 178478340, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 9-1 (0.25 g, 0.73 mMol) and 21-1 (0.13 g, 0.87 mMol) in NMP (5 mL) was added triethylamine (0.3 mL, 2.2 mMol) followed by acetic acid (0.082 mL, 1.5 mMol). After stirring at ambient temperature overnight, sodium triacetoxyborohydride (0.18 g, 0.87 mMol) was added. Upon completion, the reaction was diluted with ethyl acetate and washed with saturated NaHCO3, followed by water, then brine. The organic layer was dried with Na2SO4 and MgSO4, filtered and concentrated in vacuo to yield 21-2. LC/MS (M+1) calculated: 482.0; observed: 482.2

Aufarbeitung

  1. washwashed with saturated NaHCO3
  2. dry with materialThe organic layer was dried with Na2SO4 and MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield 21-2

Quellen und Nachweise

ORD-Eintrag
ord-1d74db5c94114f7ea0a8c5f745d49289
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008317B2

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