5-Hydroxyindoleacetic Acid → 2-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide

関与物質

役割	名称	HCID	仕込み量
反応物	5-Hydroxyindoleacetic Acid	HCID 1826	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
反応物	2-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine	HCID 90281247	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	2-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide	HCID 90281276	—

反応手順

HATU (40 mg, 0.105 mmol) was added to a solution of 2-(5-hydroxy-1H-indol-3-yl)acetic acid (19.2 mg, 0.1 mmol) and DIPEA (0.02 mL, 0.12 mmol) in DMF (0.3 mL). After 10 minutes, 9D (26.5 mg, 0.1 mmol) in 0.2 mL of DMF was added to the reaction. The reaction was stirred for 2 hours. LC/MS shows desired product with a small amount of acid. Purified reaction mixture on prep reverse phase HPLC using 20-80% B over 20 min. (A=0.1% TFA/H2O; B=0.1% TFA/Acetonitrile). Combined pure fractions as determined by LC/MS and lyophilized to provide the desired product. 1H NMR (400 MHz, CD3OD) δ 7.76 (s, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.39 (t, J=7.6 Hz, 2H), 7.21-7.01 (m, 6H), 6.96 (s, 1H), 6.84 (d, J=1.9 Hz, 1H), 6.78 (d, J=6.8 Hz, 2H), 6.68 (dd, J=8.6, 2.3 Hz, 1H), 5.46 (s, 2H), 5.21 (t, J=7.6 Hz, 1H), 2.96 (ddd, J=21.5, 13.3, 7.6 Hz, 2H); MS (m/z) 438 [M+H]+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09220710B2
出典データセット	uspto-grants-2015_12
ORD ID	ord-b9a3c52a6e754d8fb0397816574848a6
出典メモ	uspto-grants-2015_12