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

HRID 2220267Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-8bbc1d03dc1f471d91b985d1f289c681
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417065B2

Reaction notes

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