6-Hydroxynicotinamide → 6-Hydroxynicotinamide

HRID 253093Notes

Reaction equation

HRID 253093 reaction equation
[N:1]1[CH:6]=C[CH:4]=[C:3]([B:7]([OH:9])[OH:8])[CH:2]=1.[O:10]=[C:11]1[NH:16][CH:15]=[C:14]([C:17]([NH2:19])=[O:18])[CH:13]=[CH:12]1>>[N:16]1[CH:15]=[CH:14][C:13]([B:7]([OH:9])[OH:8])=[CH:12][CH:11]=1.[N:16]1[CH:4]=[C:3]([B:7]([OH:9])[OH:8])[CH:2]=[N:1][CH:6]=1.[O:10]=[C:11]1[NH:16][CH:15]=[C:14]([C:17]([NH2:19])=[O:18])[CH:13]=[CH:12]1

Participants

5

Reactant 2

HCID 729256-HydroxynicotinamideHCID 27343783-Pyridinylboronic acid

Product 3

HCID 729256-HydroxynicotinamideHCID 2734379(Pyridin-4-yl)boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acid

Procedure

The title compounds, Example 14, 15 and 16, were obtained using a procedure analogous to that described in Example 8, using pyridine-3-ylboronic acid (24 mg, 0.20 mmol), 5-bromo-1-cyclopentyl-N-(2S,3R)-4-(6-ethyl-2,2-spirocyclopentylchroman-4-ylamino)-3-hydrodroxy-1-phenylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxamide (in Ex. 14, 100 mg, 0.15 mmol); pyridine-4-ylboronic acid (26 mg, 0.21 mmol), 5-bromo-1-cyclopentyl-N-(2S,3R)-4-(6-ethyl-2,2-spirocyclopentylchroman-4-ylamino)-3-hydrodroxy-1-phenylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxamide (in Ex. 15, 105 mg, 0.16 mmol) and pyrimidin-5-ylboronic acid (13 mg, 0.10 mmol), 5-bromo-1-cyclopentyl-N-(2S,3R)-4-(6-ethyl-2,2-spirocyclopentylchroman-4-ylamino)-3-hydrodroxy-1-phenylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxamide (in Ex. 16, 50 mg, 0.08 mmol), respectively, to afford the title compound Example 14 as a light brown solid (MS m/z: 661(M+1); title compound Example 15 as a light yellow solid; and title compound Example 16 (MS m/z: 662(M+1).

Sources & evidence

ORD record
ord-cc34aa26def34616ba80b6a22f024c1c
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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