4-Methoxypyridine-3-boronic acid → 4-amino-N-ethyl-8-(4-methoxypyridin-3-yl)cinnoline-3-carboxamide

HRID 2375667Notes

Reaction equation

HRID 2375667 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][C:20]=3[O:19][CH3:18])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14]

Participants

3

Reactant 2

HCID 27625564-Methoxypyridine-3-boronic acidHCID 672286714-Amino-8-bromo-N-ethyl-cinnoline-3-carboxamide

Product 1

HCID 251334404-amino-N-ethyl-8-(4-methoxypyridin-3-yl)cinnoline-3-carboxamideYield 26%

Procedure

The title compound was prepared from 4-amino-8-bromo-N-ethyl-cinnoline-3-carboxamide (70.0 mg, 0.237 mmol) and 4-methoxy-3-pyridine boronic acid (153.0 mg, 0.3439 mmol) according to Method A except that the extraction was carried out with methylene chloride rather than ethyl acetate and the flash column was eluted with a gradient of 10to 60% methanol in dichloromethane. The concentrated product was then recrystallized from chloroform (with a few drops of methanol) and hexanes to afford the title compound as a yellow solid (19.6 mg, 26% yield). 1H NMR (300.132 MHz, CDCl3) δ 8.58 (d, J=5.7 Hz, 1H), 8.52-8.43 (bm, 1H), 8.46 (s, 1H), 7.92 (app quintet, J=4.0 Hz, 1H), 7.74 (dd, J=4.9, 0.9 Hz, 2H), 6.96 (d, J=5.8 Hz, 1H), 3.78 (s, 3H), 3.53 (dq, J=5.8, 7.3, Hz, 2H), 1.27 (t, J=7.3 Hz, 3H). MS APCI, m/z=324 (M+H). HPLC 1.42 min.

Workup

  1. extractionaccording to Method A except that the extraction
  2. washthe flash column was eluted with a gradient of 10to 60% methanol in dichloromethane
  3. customThe concentrated product was then recrystallized from chloroform (with a few drops of methanol) and hexanes

Sources & evidence

ORD record
ord-807a1b83f1b74afba57412692f61dfbe
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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