HCID 70654873, compound → HCID 70655146, compound

HRID 2091598Notes

Reaction equation

HRID 2091598 reaction equation
Br.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]3[CH2:21][CH2:20]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][C:4]=1Br.[CH3:23][C:24]1([CH3:44])[C:33]2[C:28](=[CH:29][CH:30]=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:32]=2)[C:27](=[O:43])[NH:26][CH2:25]1>>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]3[CH2:21][CH2:20]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[C:27](=[O:43])[NH:26][CH2:25][C:24]2([CH3:44])[CH3:23]

Participants

3

Reactant 2

HCID 70654873HCID 70654873, compoundHCID 706552611(2H)-Isoquinolinone, 3,4-dihydro-4,4-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Product 1

HCID 70655146HCID 70655146, compoundYield 37.2%

Procedure

General method C was applied to 4-(6-amino-5-bromopyridin-3-yl)-N-cyclopropylbenzenesulfonamide hydrobromide (92 mg, 0.25 mmol) and 4,4-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (75 mg, 0.25 mmol) to give 4-(6-amino-5-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyridin-3-yl)-N-cyclopropylbenzenesulfonamide (43 mg, 37% yield) as a white solid after purification by flash chromatography over silica gel (2-5% MeOH/DCM eluent). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.61 (s, 1H), 8.06 (d, J=8.5 Hz, 2H), 7.96-8.02 (m, 2H), 7.80 (d, J=1.5 Hz, 1H), 7.75 (dd, J=7.5, 1.5 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 6.00 (s, 2H), 3.20 (d, J=2.0 Hz, 2H), 2.06-2.18 (m, 1H), 1.33 (s, 6H), 0.33-0.55 (m, 4H); MS (EI) m/z=463.6 [M+1]+.

Sources & evidence

ORD record
ord-a6d873c0f05346d9b83231d844b240a3
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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