4-bromo-N-cyclopropylbenzenesulfonamide → HCID 60198103, compound

HRID 2091557Notes

Reaction equation

HRID 2091557 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[CH:18][C:17]=1[C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][CH:26]=1>>[NH2:15][C:16]1[C:17]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([NH2:32])=[O:33])=[CH:27][CH:26]=2)=[CH:18][C:19]([C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH:11][CH:12]3[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[CH:20][N:21]=1

Participants

3

Reactant 2

HCID 7447484-bromo-N-cyclopropylbenzenesulfonamideHCID 70655846HCID 70655846, compound

Product 1

HCID 60198103HCID 60198103, compoundYield 47.3%

Procedure

General method B was applied to 4-bromo-N-cyclopropylbenzenesulfonamide (41 mg, 0.15 mmol), 6-amino-5-(4-carbamoylphenyl)pyridin-3-ylboronic acid (53 mg, 0.15 mmol), to give 4-(2-amino-5-(4-(N-cyclopropylsulfamoyl)phenyl)pyridin-3-yl)benzamide as a white solid (29 mg, 41% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (d, J=2.3 Hz, 1H), 8.03 (br. s., 1H), 7.98 (d, J=8.3 Hz, 2H), 7.90 (d, J=8.5 Hz, 2H), 7.87 (d, J=2.5 Hz, 1H), 7.80 (d, J=8.5 Hz, 2H), 7.76 (d, J=1.5 Hz, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.37 (br. s., 1H), 6.06 (br. s., 2H), 2.06-2.13 (m, 1H), 0.42-0.50 (m, 2H), 0.35-0.42 (m, 2H); MS (EI) m/z: 409 [M+H]+.

Sources & evidence

ORD record
ord-23f4a5e58f6045908ea9b69c6452e051
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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