Cumylamine → ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate

HRID 448131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448131
[C:1]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH2:34]([O:36][C:37]([N:39]1[C:43]2[S:44][C:45]([C:47](O)=[O:48])=[CH:46][C:42]=2[C:41]([NH:50][C:51](=[O:64])[C:52]2[CH:57]=[CH:56][C:55]([N:58]3[CH2:63][CH2:62][O:61][CH2:60][CH2:59]3)=[CH:54][CH:53]=2)=[N:40]1)=[O:38])[CH3:35].CCN(C(C)C)C(C)C>CN(C)C=O.O>[CH3:2][C:1]([NH:10][C:47]([C:45]1[S:44][C:43]2[N:39]([C:37]([O:36][CH2:34][CH3:35])=[O:38])[N:40]=[C:41]([NH:50][C:51](=[O:64])[C:52]3[CH:57]=[CH:56][C:55]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)=[CH:54][CH:53]=3)[C:42]=2[CH:46]=1)=[O:48])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3]

Komponenten

7

Edukt 4

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667857921-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride

Produkt 1

HCID 44520544ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of cumylamine (1.43 g, 10.6 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 3.40 g, 10.6 mmol), 1-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride (3.40 mg, 7.07 mmol) and N,N′-diisopropylethylamine (12.1 mL, 7.07 mmol) in 80 mL of dimethylformamide was stirred at room temperature for 20 hours. Afterward the reaction mixture was diluted with water and extracted with dichloromethane. Volatiles were removed by evaporation under reduced pressure and the residue was triturated with ethyl acetate, filtered, extensively washed with diethyl ether and dried under vacuum at 40° C., to give 3.7 g of the title compound, used in the next step without further purification.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. customVolatiles were removed by evaporation under reduced pressure
  3. customthe residue was triturated with ethyl acetate
  4. filtrationfiltered
  5. washextensively washed with diethyl ether
  6. customdried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-29db0bf3015440778be39bfe1ff617d1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481584B2

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