Triethylamine → 2-(7-Chloro-1h-benzimidazol-1-yl)-n-[4-(1-cyano-1-methylethyl)-3-fluorobenzyl]acetamide

HRID 419993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419993
[Cl:1][C:2]1[C:7]2[N:8]([CH2:11][C:12]([OH:14])=O)[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:28])([CH3:27])[C:25]#[N:26])=[C:20]([F:29])[CH:19]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[C:7]2[N:8]([CH2:11][C:12]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([C:25]#[N:26])([CH3:28])[CH3:27])=[C:20]([F:29])[CH:19]=3)=[O:14])[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11206606(7-Chloro-1H-benzimidazol-1-yl)acetic acidHCID 666493672-[4-(Aminomethyl)-2-fluorophenyl]-2-methylpropanenitrile hydrochloride

Produkt 1

HCID 598042572-(7-Chloro-1h-benzimidazol-1-yl)-n-[4-(1-cyano-1-methylethyl)-3-fluorobenzyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(7-Chloro-1H-benzimidazol-1-yl)-N-[4-(1-cyano-1-methylethyl)-3-fluorobenzyl]acetamide is synthesized according to example 14 with (7-chloro-1H-benzimidazol-1-yl)acetic acid (150 mg, 0.712 mmol) prepared according to scheme 1, and 2-[4-(aminomethyl)-2-fluorophenyl]-2-methylpropanenitrile hydrochloride (196 mg, 0.855 mmol) prepared according to scheme 8, Et3N (238 μL, 1.71 mmol) and HATU (325 mg, 0.855 mmol) in DMF (3.0 mL). The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (50 21.2×50 mm, Mobile phase: A=water (0.075% TFA) B=MeCN (0.075% TFA). Yield=14 mg as TFA salt, 0.035 mmol, 5%); 1H NMR (400 MHz, DMSO-D6) δ ppm 1.67 (s, 6H), 4.30 (d, J=5.86 Hz, 2H), 5.24 (s, 2H), 7.10-7.22 (m, 3H), 7.23-7.28 (m, 1H), 7.38 (t, J=8.40 Hz, 1 H), 7.62 (d, J=7.81 Hz, 1H), 8.31 (s, 1H), 8.81 (s, 1H). MS [M+H], calcd: 385.1. found: 385.0.

Aufarbeitung

  1. customprepared
  2. customprepared
  3. customThe product is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6214f5543d874bb78be07810d2261836
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093402B2

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