Diisopropylethylamine → HCID 71208954, Verbindung

HRID 1887800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887800
[Br:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:46][CH2:47][C:48]1[C:57](=[O:58])[C:56]2[C:51](=[CH:52][C:53]([Cl:59])=[CH:54][CH:55]=2)[N:50]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:49]=1>C(Cl)Cl>[Cl:59][C:53]1[CH:52]=[C:51]2[C:56]([C:57](=[O:58])[C:48]([CH2:47][NH:46][C:7]([C:4]3[S:3][C:2]([Br:1])=[N:6][CH:5]=3)=[O:9])=[CH:49][N:50]2[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:55][CH:54]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27632102-Bromothiazole-5-carboxylic acidHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one2×

Produkt 1

HCID 71208954HCID 71208954, VerbindungAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2-bromothiazole-5-carboxylic acid (241 mg, 1.16 mmol) and N,N-diisopropylethylamine (409 mg, 552 μL, 3.16 mmol) in methylene chloride was added (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (559 mg, 1.26 mmol). After 15 min., 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (300 mg, 1.05 mmol) was added. The reaction mixture was stirred at room temperature. The mixture was diluted with CH2Cl2 and washed with water followed by 1N aqueous HCl and finally saturated aqueous sodium carbonate solution. The organic layer was dried (Na2SO4), filtered and concentrated. The product 2-bromo-thiazole-5-carboxylic acid (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide (464 mg, 93%) was obtained without further purification.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-915f40b7f8a144e9bf13b5a35675f697
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501732B2

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