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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 410943Generated: November 2, 2026

2-Methoxyethylamine → 1-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide

https://huagongshe.com/reaction/410943

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-MethoxyethylamineHCID 8018—
ReactantDiisopropylethylamineHCID 81531—
ReactantMethanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733084—
Reactant1-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acidHCID 86656877—
SolventDimethylformamideHCID 6228—
Product1-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amideHCID 8665687840.5%

Reaction Steps

1-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide (61.0 mg) was prepared by following General Procedure F starting from 1-ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid (133.0 mg), 2-methoxy-ethylamine (38.0 mg), HBTU (200.0 mg) and DIEA (0.2 mL) in DMF (1.0 mL). LCMS: m/z 490. 1H NMR (DMSO-d6, 400 MHz): δ 8.44 (1H, m), 8.38-8.32 (2H, m), 8.07 (1H, m), 7.76-7.68 (2H, m), 7.51-7.45 (1H, m), 7.40-7.39 (2H, m), 7.12-7.10 (1H, m), 4.20-4.17 (2H, m), 3.48-3.42 (3H, m), 3.26 (3H, s), 1.48-1.46 (1H, m), 1.32-1.28 (3H, t), 2 —NH proton signals were not observed.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08759535B2
Source datasetuspto-grants-2014_06
ORD IDord-6d88ca22b89346f3809f21d3ccee8d89
Source noteuspto-grants-2014_06