Diisopropylethylamine → 2-{[3-(morpholin-4-ylsulfonyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

HRID 1025474

Reaktionsgleichung

Reaktionsgleichung von HRID 1025474
[NH2:1][C:2]1[S:3][C:4]2[CH2:26][CH2:25][CH2:24][CH2:23][C:5]=2[C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)=[O:8].[N:27]1([S:33]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39](O)=[O:40])(=[O:35])=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:27]1([S:33]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39]([NH:1][C:2]2[S:3][C:4]3[CH2:26][CH2:25][CH2:24][CH2:23][C:5]=3[C:6]=2[C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)=[O:8])=[O:40])(=[O:35])=[O:34])[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2574763-(Morpholine-4-sulfonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682078332-amino-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

Produkt 1

HCID 712384872-{[3-(morpholin-4-ylsulfonyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamideAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 9.1 mg of 2-amino-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, 8.1 mg of 3-(morpholine-4-sulfonyl)benzoic acid, 0.016 mL of N,N-diisopropylethylamine, and 0.5 mL of DMF was added a mixture of 11.4 mg of HATU and 0.1 mL of DMF, followed by stirring at 60° C. overnight. The reaction mixture was separated by the addition of chloroform and water, and then the organic layer was concentrated under reduced pressure. The obtained residue was purified by preparative high performance liquid chromatography (methanol-0.1% aqueous formic acid solution) to obtain 8.9 mg of 2-{[3-(morpholin-4-ylsulfonyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide.

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was separated by the addition of chloroform and water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by preparative high performance liquid chromatography (methanol-0.1% aqueous formic acid solution)

Quellen und Nachweise

ORD-Eintrag
ord-fe82e848ec974b0d86516fe30451cd60
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729068B2

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