6-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one → 6'-amino-N-ethyl-N,4-dimethyl-5'-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3'-bipyridine]-5-sulfonamide

HRID 2091569Notes

Reaction equation

HRID 2091569 reaction equation
[CH2:1]([N:3]([CH3:18])[S:4]([C:7]1[CH:8]=[N:9][C:10]([Sn](C)(C)C)=[CH:11][C:12]=1[CH3:13])(=[O:6])=[O:5])[CH3:2].[NH2:19][C:20]1[C:25]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[C:32](=[O:36])[NH:31][CH2:30][CH2:29]3)=[CH:24][C:23](Br)=[CH:22][N:21]=1>>[NH2:19][C:20]1[N:21]=[CH:22][C:23]([C:10]2[CH:11]=[C:12]([CH3:13])[C:7]([S:4]([N:3]([CH2:1][CH3:2])[CH3:18])(=[O:6])=[O:5])=[CH:8][N:9]=2)=[CH:24][C:25]=1[C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32](=[O:36])[NH:31][CH2:30][CH2:29]2

Participants

3

Reactant 2

HCID 682933526-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-oneHCID 70655238N-ethyl-N,4-dimethyl-6-(trimethylstannyl)pyridine-3-sulfonamide

Product 1

HCID 706547796'-amino-N-ethyl-N,4-dimethyl-5'-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3'-bipyridine]-5-sulfonamideYield 33%

Procedure

General method D was applied to N-ethyl-N,4-dimethyl-6-(trimethylstannyl)pyridine-3-sulfonamide (226 mg, 0.6 mmol) and 6-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (190 mg, 0.6 mmol) to give 6′-amino-N-ethyl-N,4-dimethyl-5′-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3′-bipyridine]-5-sulfonamide as a yellow solid (41 mg, 33% yield) after purification by reverse phase preparatory HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.84-8.88 (m, 2H), 8.56 (s, 1H), 8.23 (s, 1H), 8.06 (br. s., 1H), 8.00 (d, J=7.8 Hz, 1H), 7.49-7.56 (m, 2H), 3.38-3.48 (m, 2H), 3.23 (q, J=7.0 Hz, 2H), 3.00 (t, J=6.3 Hz, 2H), 2.81 (s, 3H), 2.61 (s, 3H), 1.09 (t, J=7.0 Hz, 3H); MS (EI) m/z=452.5 [M+1]+.

Sources & evidence

ORD record
ord-f8538d0fc44a467290620deb4b5ce559
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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