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

HRID 2091568Notes

Reaction equation

HRID 2091568 reaction equation
[CH:1]1([CH2:4][N:5]([CH3:19])[S:6]([C:9]2[CH:10]=[N:11][C:12]([Sn](C)(C)C)=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:3][CH2:2]1.[NH2:20][C:21]1[C:26]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[C:33](=[O:37])[NH:32][CH2:31][CH2:30]3)=[CH:25][C:24](Br)=[CH:23][N:22]=1>>[NH2:20][C:21]1[N:22]=[CH:23][C:24]([C:12]2[CH:13]=[CH:14][C:9]([S:6]([N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[CH3:19])(=[O:8])=[O:7])=[CH:10][N:11]=2)=[CH:25][C:26]=1[C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33](=[O:37])[NH:32][CH2:31][CH2:30]2

Participants

3

Reactant 2

HCID 682933526-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-oneHCID 70655068N-(cyclopropylmethyl)-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide

Product 1

HCID 706549646'-amino-N-(cyclopropylmethyl)-N-methyl-5'-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3'-bipyridine]-5-sulfonamideYield 46%

Procedure

General method D was applied to N-(cyclopropylmethyl)-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide (233 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-(cyclopropylmethyl)-N-methyl-5′-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3′-bipyridine]-5-sulfonamide as a yellow solid (127 mg, 0.27 mmol, 46% yield) after purification by reverse phase preparatory HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.87 (d, J=1.5 Hz, 1H), 8.84 (d, J=2.3 Hz, 1H), 8.05-8.19 (m, 3H), 7.90-7.98 (m, 2H), 7.43-7.50 (m, 2H), 6.34 (s, 2H), 3.38-3.45 (m, 2H), 2.97 (t, J=1.0 Hz, 2H), 2.91 (d, J=6.8 Hz, 2H), 2.80 (s, 3H), 0.85-0.96 (m, 1H), 0.43-0.51 (m, 2H), 0.16-0.21 (m, 2H); MS (EI) m/z=464.5 [M+1]+.

Sources & evidence

ORD record
ord-fc86679c9b9347c6916866a38a5f92c7
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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