Triethylamine → tert-Butyl 2-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

HRID 500912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500912
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14](Cl)=[O:15])[S:13][C:6]=12.Cl.[C:25]([N:32](C)[CH2:33][CH2:34][NH2:35])([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([NH:35][CH2:34][CH2:33][NH:32][C:25](=[O:26])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:15])[S:13][C:6]=12

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 45072251tert-Butyl (2-aminoethyl)methylcarbamate--hydrogen chloride (1/1)HCID 594245267-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbonyl chloride

Produkt 1

HCID 59424685tert-Butyl 2-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 40 (shown in the scheme 7, 100 mg, 0.26 mmol), N-Boc-N-methylethylenediamine hydrochloride (50 mg, 0.26 mmol) and Et3N (36 μL, 0.52 mmol) in DCM (2 mL) was stirred for 4 h at room temperature and diluted with EtOAc (10 mL). The combined mixture was washed with brine and phases were separated. The aqueous phase was extracted with EtOAc, and the extract was combined with the organic phase, dried over anhydrous Na2SO4 and concentrated to afford title compound 292 (119 mg, 96%, crude) as yellowish solid. MS (m/z): 477.1 (M+H) (found).

Aufarbeitung

  1. washThe combined mixture was washed with brine and phases
  2. customwere separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9cdd4f5b886c4d29b9eeaec73fc617a5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772247B2

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