1-(4,6-Dichloro-1,5-naphthyridin-3-yl)-2-methylpropan-1-one → 1-(6-Chloro-4-((4-((dimethylamino)methyl)cyclohexyl)amino)-1,5-naphthyridin-3-yl)-2-methylpropan-1-one

HRID 526260Notes

Reaction equation

HRID 526260 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:17])[CH:14]([CH3:16])[CH3:15].[CH3:18][N:19]([CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([NH2:28])[CH2:24][CH2:23]1)[CH3:20]>>[Cl:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:2]2[NH:28][CH:25]1[CH2:26][CH2:27][CH:22]([CH2:21][N:19]([CH3:20])[CH3:18])[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 1177728531-(4,6-Dichloro-1,5-naphthyridin-3-yl)-2-methylpropan-1-oneHCID 178483674HCID 178483674, compound

Product 1

HCID 716675031-(6-Chloro-4-((4-((dimethylamino)methyl)cyclohexyl)amino)-1,5-naphthyridin-3-yl)-2-methylpropan-1-oneYield 89%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)-2-methylpropan-1-one (500 mg, 1.85 mmol) was reacted with trans-4-((dimethylamino)methyl)cyclohexanamine (436 mg, 2.78 mmol) to afford the product (640 mg, 89%) as a white solid: ESI MS m/z 389 [M+H]+.

Sources & evidence

ORD record
ord-4035124f4b334a728147ef2bbe2ad314
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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