Sodium Carbonate → 4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-ethyl-N,2-dimethylbenzenesulfonamide

HRID 2091589Notes

Reaction equation

HRID 2091589 reaction equation
[CH2:1]([N:3]([CH3:23])[S:4]([C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][C:8]=1[CH3:22])(=[O:6])=[O:5])[CH3:2].[NH2:24][C:25]1[C:26]([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[C:38](=[O:42])[NH:37][CH2:36][CH2:35]3)=[N:27][C:28](Br)=[CH:29][N:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CCC>[NH2:24][C:25]1[N:30]=[CH:29][C:28]([C:10]2[CH:11]=[CH:12][C:7]([S:4]([N:3]([CH2:1][CH3:2])[CH3:23])(=[O:5])=[O:6])=[C:8]([CH3:22])[CH:9]=2)=[N:27][C:26]=1[C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[C:38](=[O:42])[NH:37][CH2:36][CH2:35]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70655640N-ethyl-2,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamideHCID 866702106-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 706548804-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-ethyl-N,2-dimethylbenzenesulfonamideYield 29%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of N-ethyl-2,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (140 mg, 0.42 mmol), 6-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (150 mg, 0.38 mmol) Pd(PPh3)4 (13.2 mg, 0.011 mmol) and 2.0 M aq. Na2CO3 (0.38 mL) in n-butanol (2 mL) was microwave heated at 150° C. for 10 min to provide 4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-ethyl-N,2-dimethylbenzenesulfonamide (49 mg, 29% yield) after purification by reverse phase preparatory HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69 (s, 1H), 8.04 (s, 1H), 7.93-8.02 (m, 3H), 7.82 (d, J=8.28 Hz, 1H), 7.67-7.77 (m, 2H), 6.62 (s, 2H), 3.43 (td, J=6.40, 2.51 Hz, 2H), 3.18 (q, J=6.94 Hz, 3H), 3.00 (t, J=6.53 Hz, 2H), 2.76 (s, 3H), 2.59 (s, 3H), 1.08 (t, J=7.15 Hz, 3H). MS (EI) m/z: 452 [M+H]+. HPLC (Sunfire C18 4.6 mm×50 mm, 10-90% MeCN:10 mM aq NH4OAc, 4 min gradient) tR=2.14 min, 100% integrated area.

Sources & evidence

ORD record
ord-42cf07d008f34df2bc00f0fb7cc97b94
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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