Triethylamine → tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate

HRID 1805284

Reaktionsgleichung

Reaktionsgleichung von HRID 1805284
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][N:25]=1>CC#N>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:29])=[CH:26][N:25]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Produkt 1

HCID 57717462tert-Butyl 2-(6-chloronicotinamido)phenylcarbamateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To solution of (2-amino-phenyl)-carbamic acid tert-butyl ester (22) (Seto, C. T.; Mathias, J. P.; Whitesides, G. M.; J. Amer. Chem. Soc., (1993), 115, 1321-1329.) (1.56 g, 7.49 mmol) in MeCN (40 mL) is added triethylamine (2.60 mL, 18.7 mmol) and 6-chloronicotinic acid (1.42 g 8.99 mmol). The mixture is stirred for 18 h at r.t. Upon completion of the reaction, the solvent is removed in vacuo and the residue is partitioned between EtOAc and an NH4Cl solution. The organic phase is collected and the aqueous layer is then extracted with EtOAc; the combined organic layers are washed with brine, dried over MgSO4 and evaporated. The residue is purified by flash chromatography using EtOAc/Hexane (a gradient of 20:80 to 50:50) as an eluent, to afford the title compound 94 (2.39 g, 92% yield). 1H NMR (DMSO-d6) δ(ppm): 10.01 (s, 1H), 8.96 (d, J=2.0 Hz, 1H), 8.71 (s, 1H), 8.35 (dd, J=8.4, 2.4 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.22 (td, J=7.8, 1.4 Hz, 1H), 7.13 (t, J=7.6 Hz, 1H), 1.44 (s, 9H). LRMS (ESI): (calc) 347.10 (found) 370.1 (M+Na+).

Aufarbeitung

  1. customUpon completion of the reaction
  2. customthe solvent is removed in vacuo
  3. customthe residue is partitioned between EtOAc
  4. customThe organic phase is collected
  5. extractionthe aqueous layer is then extracted with EtOAc
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a9aba65ecf4341d682b831860b10ce5b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354445B2

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