Diisopropylethylamine → HCID 24953975, Verbindung

HRID 870058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870058
[CH3:1][C:2]1[S:3][C:4]([CH3:21])=[C:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:6]=1[C:7](O)=[O:8].[Cl-].[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([C@@H:33]([NH3+:35])[CH3:34])=[CH:29][CH:28]=1)=[O:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[S:3][C:4]([CH3:21])=[C:5]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)[C:6]=1[C:7]([NH:35][C@H:33]([C:30]1[CH:31]=[CH:32][C:27]([C:25]([O:24][CH3:23])=[O:26])=[CH:28][CH:29]=1)[CH3:34])=[O:8]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 451407862,5-Dimethyl-4-(4-(trifluoromethyl)benzyl)thiophene-3-carboxylic acidHCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

Produkt 1

HCID 24953975HCID 24953975, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxylic acid from Example 11, Step 4 (4.36 g, 1 eq.) and (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride from Example 1, Step 9 (3.29 g, 1.10 eq.) in dimethylformamide (50 mL) is added HATU (5.65 g, 1.07 eq.) in one portion. After stirring for 2 minutes, diisopropylethylamine (6.0 mL, 2.5 eq.) was added in one portion and the reaction stirred until consumption of the starting acid. The reaction was poured onto half-saturated sodium bicarbonate (400 mL) and the white suspension stirred vigorously for 30 minutes. The solids were collected by filtration, washed with water while onto the Buchner, dried and purified by chromatography on silica gel (2:98 to 10:90 EtOAc/CHCl3) to afford the desired product as a white solid. MS (+APCI): m/z 476 (M+1)+.

Aufarbeitung

  1. stirringthe reaction stirred until consumption of the starting acid
  2. stirringthe white suspension stirred vigorously for 30 minutes
  3. filtrationThe solids were collected by filtration
  4. washwashed with water while onto the Buchner
  5. customdried
  6. custompurified by chromatography on silica gel (2:98 to 10:90 EtOAc/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-33e4e4218cb1454eac84d0e4a895c616
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969394B2

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