2,8-Dichloro-7-(methylsulfonyl)-1,5-naphthyridine → HCID 178483672, compound

HRID 526179Notes

Reaction equation

HRID 526179 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.C(O)(=O)C.C(O)(=O)C.[CH3:25][N:26]([CH2:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31][CH2:30]1)[CH3:27]>>[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:35][C@H:32]1[CH2:33][CH2:34][C@H:29]([CH2:28][N:26]([CH3:27])[CH3:25])[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 1177730332,8-Dichloro-7-(methylsulfonyl)-1,5-naphthyridineHCID 178476567HCID 178476567, compound

Product 1

HCID 178483672HCID 178483672, compoundYield 70%

Procedure

Following general procedure I, 2,8-dichloro-7-(methylsulfonyl)-1,5-naphthyridine (150 mg, 0.54 mmol) was reacted with trans-4-[(dimethylamino)methyl]cyclohexanamine diacetic acid salt (190 mg, 0.68 mmol) to afford the desired product (150 mg, 68%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.84 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.70-7.60 (m, 1H), 7.57 (d, J=8.8 Hz, 1H), 5.05-4.95 (m, 1H), 3.09 (s, 3H), 2.34-2.24 (m, 8H), 2.18 (d, J=7.0 Hz, 2H), 2.00-1.92 (m, 2H), 1.57-1.50 (m, 1H), 1.42-1.30 (m, 2H), 1.24-1.12 (m, 2H); ESI MS m/z 397 [M+H]+

Sources & evidence

ORD record
ord-77a7319bc3a54aacb70cfc80c6ca089d
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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