2-(2-amino-5-bromopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one → 6'-amino-N-ethyl-N-methyl-5'-(6-oxo-5,6-dihydro-4H-thieno[2,3-c]pyrrol-2-yl)-[2,3'-bipyridine]-5-sulfonamide

HRID 2091566Notes

Reaction equation

HRID 2091566 reaction equation
[CH2:1]([N:3]([CH3:17])[S:4]([C:7]1[CH:8]=[N:9][C:10]([Sn](C)(C)C)=[CH:11][CH:12]=1)(=[O:6])=[O:5])[CH3:2].[NH2:18][C:19]1[C:24]([C:25]2[S:33][C:28]3[C:29](=[O:32])[NH:30][CH2:31][C:27]=3[CH:26]=2)=[CH:23][C:22](Br)=[CH:21][N:20]=1>>[NH2:18][C:19]1[N:20]=[CH:21][C:22]([C:10]2[CH:11]=[CH:12][C:7]([S:4]([N:3]([CH2:1][CH3:2])[CH3:17])(=[O:6])=[O:5])=[CH:8][N:9]=2)=[CH:23][C:24]=1[C:25]1[S:33][C:28]2[C:29](=[O:32])[NH:30][CH2:31][C:27]=2[CH:26]=1

Participants

3

Reactant 2

HCID 706549922-(2-amino-5-bromopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-oneHCID 70655349N-ethyl-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide

Product 1

HCID 706546026'-amino-N-ethyl-N-methyl-5'-(6-oxo-5,6-dihydro-4H-thieno[2,3-c]pyrrol-2-yl)-[2,3'-bipyridine]-5-sulfonamideYield 38%

Procedure

General method D was applied to N-ethyl-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide (218 mg, 0.6 mmol) and 2-(2-amino-5-bromopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one (186 mg, 0.6 mmol) to give 6′-amino-N-ethyl-N-methyl-5′-(6-oxo-5,6-dihydro-4H-thieno[2,3-c]pyrrol-2-yl)-[2,3′-bipyridine]-5-sulfonamide as a yellow solid (94 mg, 38% yield) after purification by preparatory reverse phase HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.91 (d, J=1.5 Hz, 1H), 8.87 (d, J=2.3 Hz, 1H), 8.44 (s, 1H), 8.26 (d, J=2.3 Hz, 1H), 8.10-8.20 (m, 2H), 7.43 (s, 1H), 6.65 (s, 2H), 4.35 (s, 2H), 3.30 (s, 4H), 3.09 (dd, J=14.3, 7.0 Hz, 2H), 2.72 (s, 3H), 1.06 (t, J=7.0 Hz, 3H); MS (EI) m/z=430 [M+1]+.

Sources & evidence

ORD record
ord-47bdc4432fbf4ebeb97e916dcff16938
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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