5-Aminocarbonylpyridine-2-boronic acid → HCID 70654610, compound

HRID 2091558Notes

Reaction equation

HRID 2091558 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]3[CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1Br.[C:22]([C:25]1[CH:26]=[CH:27][C:28](B(O)O)=[N:29][CH:30]=1)(=[O:24])[NH2:23]>>[NH2:1][C:2]1[C:3]([C:28]2[CH:27]=[CH:26][C:25]([C:22]([NH2:23])=[O:24])=[CH:30][N:29]=2)=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14](=[O:16])(=[O:15])[NH:17][CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 577474035-Aminocarbonylpyridine-2-boronic acidHCID 70654595HCID 70654595, compound

Product 1

HCID 70654610HCID 70654610, compoundYield 28.1%

Procedure

General method B was applied to 4-(6-amino-5-bromopyridin-3-yl)-N-cyclopropylbenzenesulfonamide (112 mg, 0.304 mmol) and 5-carbamoylpyridin-2-ylboronic acid (75 mg, 0.453 mmol) to provide 2′-amino-5′-(4-(N-cyclopropylsulfamoyl)phenyl)-[2,3′-bipyridine]-5-carboxamide as a white solid (35 mg, 28% yield) after purification by reverse phase preparatory HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07-9.16 (m, 1H), 8.53 (d, J=2.3 Hz, 1H), 8.47 (d, J=2.3 Hz, 1H), 8.32 (dd, J=14.1, 10.8 Hz, 2H), 8.21 (br. s., 1H), 8.01 (d, J=8.5 Hz, 2H), 7.91 (d, J=2.5 Hz, 1H), 7.85 (d, J=8.3 Hz, 2H), 7.79 (br. s., 2H), 7.61 (br. s., 1H), 2.06-2.18 (m, 1H), 0.34-0.55 (m, 4H); MS (EI) m/z: 410 [M+H]+.

Sources & evidence

ORD record
ord-3051e606298f40e087052553432c07d8
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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