2,7-Naphthyridin-1(2H)-one, 3,4-dihydro-6-(trimethylstannyl)- → HCID 70654976, compound

HRID 2091608Notes

Reaction equation

HRID 2091608 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([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)=[N:6][C:7]=1Br.C[Sn](C)(C)[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][N:33]=1)[C:30](=[O:34])[NH:29][CH2:28][CH2:27]2>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([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)=[N:6][C:7]=1[C:24]1[N:33]=[CH:32][C:31]2[C:30](=[O:34])[NH:29][CH2:28][CH2:27][C:26]=2[CH:25]=1

Participants

5

Reactant 2

HCID 706546602,7-Naphthyridin-1(2H)-one, 3,4-dihydro-6-(trimethylstannyl)-HCID 86670221HCID 86670221, compound

Product 1

HCID 70654976HCID 70654976, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(5-amino-6-bromopyrazin-2-yl)-N-cyclopropylbenzenesulfonamide (150 mg, 0.41 mmol), 6-(trimethylstannyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one (150 mg, 0.48 mmol) and Pd(PPh3)4 (23 mg, 0.02 mmol) in dioxane (2 mL) was heated in the microwave 20 min at 150° C. At completion, the reaction mixture was purified by reverse phase preparatory HPLC to provide 4-(5-amino-6-(8-oxo-5,6,7,8-tetrahydro-2,7-naphthyridin-3-yl)pyrazin-2-yl)-N-cyclopropylbenzenesulfonamide (8 mg, 5% yield) as an orange solid after lyophilization. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (s, 1H), 8.87 (s, 1H), 8.59 (s, 1H), 8.35 (d, J=8.5 Hz, 2H), 8.17 (br. s., 1H), 7.84-7.99 (m, 3H), 3.51 (t, 2H), (t, J=6.3 Hz, 2H), 0.29-0.57 (m, 4 H); MS (EI) m/z=437.5 [M+1]+.

Workup

  1. customAt completion, the reaction mixture was purified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-868c13164a2f46839db43952ec204881
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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