Sodium Bicarbonate → 4-(2-Oxo-4-(2-(6-(trifluoromethyl)-1H-indol-1-yl)acetyl)piperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

HRID 2043141

Reaktionsgleichung

Reaktionsgleichung von HRID 2043141
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[S:19][CH:20]=[CH:21][N:22]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[CH:30][N:31]2[CH2:34][C:35](O)=[O:36])=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+].Cl.S1C(N)=NC=N1>>[O:1]=[C:2]1[CH2:7][N:6]([C:35](=[O:36])[CH2:34][N:31]2[C:32]3[C:28](=[CH:27][CH:26]=[C:25]([C:24]([F:38])([F:23])[F:39])[CH:33]=3)[CH:29]=[CH:30]2)[CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17][C:18]2[S:19][CH:20]=[CH:21][N:22]=2)(=[O:16])=[O:15])=[CH:12][CH:13]=1

Komponenten

6

Edukt 5

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220145431,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1)HCID 594656314-(2-Oxopiperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamideHCID 670827152-(6-(trifluoromethyl)-1H-indol-1-yl)acetic acid

Produkt 1

HCID 536276154-(2-Oxo-4-(2-(6-(trifluoromethyl)-1H-indol-1-yl)acetyl)piperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamideAusbeute 34,5 %

Versuchsvorschrift

Synthesized according to general procedure 14, method A. The reaction was set up with 4-(2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (100 mg, 0.29 mmol), 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetic acid (71 mg, 0.29 mmol), HATU reagent (220 mg, 0.58 mmol), sodium bicarbonate (74 mg, 0.87 mmol), and DMF/CH2Cl2—1/1 (0.50 mL) to obtain the desired amide as a white solid (55 mg, 0.10 mmol, 34% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.78 (s, 1H), 7.91 (s, 1H), 7.85 (d, J=8.4 Hz, 2H), 7.75 (d, J=8.3 Hz, 1H), 7.58 (dd, J=5.1, 8.4 Hz, 2H), 7.52-7.48 (m, 1H), 7.32-7.27 (m, 2H), 6.85 (d, J=4.6 Hz, 1H), 6.61 (d, J=2.9 Hz, 1H), 5.40 (d, J=9.8 Hz, 2H), 4.49 (s, 1H), 4.22 (s, 1H), 4.01 (s, 2H), 3.81 (s, 2H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=564.4; tR=3.17 min.

Aufarbeitung

  1. customSynthesized

Quellen und Nachweise

ORD-Eintrag
ord-b8f8da1df2bf401697cf8aec6b6c2694
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586589B2

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