Sodium Bicarbonate → tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamate

HRID 1727370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727370
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=O.C1([CH2:33][CH2:34][C:35]([NH2:37])=[S:36])C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:12][C:8]1[CH:7]=[C:6]([C:4]2[N:37]=[C:35]([CH2:34][CH3:33])[S:36][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=2)[CH:11]=[CH:10][CH:9]=1.[NH2:19][C:15]1[CH:14]=[C:13]([C:3]2[S:36][C:35]([CH2:34][CH3:33])=[N:37][C:4]=2[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=2)[CH:18]=[CH:17][N:16]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 51507353-PhenylpropanethioamideHCID 229326522-Bromo-1-(3-bromophenyl)-2-[2-(boc-amino)-4-pyridyl]ethanone hydrocbromide

Produkt 2

HCID 229326504-[4-(3-Bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-amineAusbeute 8 %HCID 22932827tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-1-(3-bromophenyl)-2-[2-(tert-butoxycarbonylamino)-4-pyridyl]ethanone hydrobromide (22 g, 51 mmol) in N,N,-dimethylformamide (100 mL) was added thiopropionamide (4.3 g, 49 mmol), and the mixture was stirred for 2 hours at room temperature. Into the reaction mixture was poured an aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with water, then, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1), then, recrystallized from hexane-ethyl acetate to obtain 4-(3-bromophenyl)-5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-1,3-thiazole (6.0 g, yield 27%) and 5-(2-amino-4-pyridyl)-4-(3-bromophenyl)-2-ethyl-1,3-thiazole (1.4 g, yield 8%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)
  6. customrecrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-df244dbe4b4645d3b895abdf2477d0b3
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

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