Triethylamine → 3-{[2-(2-Trifluoromethyl-biphenyl-4-yl)-thieno[2,3-b]pyridin-5-ylmethyl]-amino}-propionic acid

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Reaktionsgleichung

[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[C:7]([C:9]2[S:19][C:12]3=[N:13][CH:14]=[C:15]([CH:17]=O)[CH:16]=[C:11]3[CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.[NH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33].C(N(CC)CC)C.[BH4-].[Na+]>CO>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:8]=[C:7]([C:9]2[S:19][C:12]3=[N:13][CH:14]=[C:15]([CH2:17][NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:16]=[C:11]3[CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 2-(2-trifluoromethyl-biphenyl-4-yl)-thieno[2,3-b]pyridine-5-carbaldehyde (32 mg, 0.083 mmol) in MeOH (2 mL) is added β-alanine HCl salt (37 mg, 0.42 mmol) and triethylamine (23 uL, 0.16 mmol). The mixture is stirred at 50° C. for 20 minutes. Sodium borohydride (30 mg, 0.8 mmol) is added at room temperature and it is stirred for 10 minutes. The mixture is purified with preparative LCMS to give 22 mg of 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-thieno[2,3-b]pyridin-5-ylmethyl]-amino}-propionic acid, which is converted to HCl salt: 1H NMR (400 MHz, CD3OD) δ 8.56 (d, 1 H), 8.30 (d, 1 H), 8.08 (d, 1 H), 7.98 (dd, 1 H), 7.84 (s, 1 H), 7.42 (d, 1 H), 7.40-7.34 (m, 3 H), 7.30-7.24 (m, 2 H); MS (ES) 457.1 (M+H+).

Aufarbeitung

stirringit is stirred for 10 minutes
customThe mixture is purified with preparative LCMS

Quellen und Nachweise

ORD-Eintrag: ord-8bbc1d03dc1f471d91b985d1f289c681
Quelldatensatz: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07417065B2

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