2,8-Dichloro-7-(methylsulfonyl)-1,5-naphthyridine → HCID 178484104, compound

HRID 526180Notes

Reaction equation

HRID 526180 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5](Cl)[C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][N:8]=2)[N:3]=1.Cl.Cl.[CH3:19][N:20]([CH3:28])[C@H:21]1[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]1>>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:27][C@H:24]1[CH2:25][CH2:26][C@H:21]([N:20]([CH3:28])[CH3:19])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 1177730332,8-Dichloro-7-(methylsulfonyl)-1,5-naphthyridineHCID 178484109HCID 178484109, compound

Product 1

HCID 178484104HCID 178484104, compoundYield 34.2%

Procedure

Following general procedure I, 2,8-dichloro-7-(methylsulfonyl)-1,5-naphthyridine (140 mg, 0.52 mmol) was reacted with trans-N1,N1-dimethylcyclohexane-1,4-diamine dihydrochloride (140 mg, 0.65 mmol) to afford the desired product (68 mg, 34%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 8.85 (s, 1H), 8.15 (d, J=8.8 Hz, 1H), 7.66 (d, J=7.7 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 5.06-4.96 (m, 1H), 3.09 (s, 3H), 2.33 (s, 6H), 2.33-2.28 (m, 2H), 2.27-2.17 (m, 1H), 2.06-1.99 (m, 2H), 1.56-1.32 (m, 4H); ESI MS m/z 383 [M+H]+

Sources & evidence

ORD record
ord-d7d64525d94e4091bd86921bd3123b9b
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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