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

HRID 2178960Notes

Reaction equation

HRID 2178960 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:16])[CH2:14][CH3:15].[CH3:17][N:18]([CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]1)[CH3:19]>>[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:16])[CH2:14][CH3:15])=[C:2]2[NH:27][CH:24]1[CH2:25][CH2:26][CH:21]([CH2:20][N:18]([CH3:19])[CH3:17])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 897056421-(4,6-Dichloro-1,5-naphthyridin-3-yl)propan-1-oneHCID 178483674HCID 178483674, compound

Product 1

HCID 1177739911-(6-Chloro-4-((4-((dimethylamino)methyl)cyclohexyl)amino)-1,5-naphthyridin-3-yl)propan-1-oneYield 93.4%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)propan-1-one (255 mg, 1.0 mmol) was reacted with trans-4-((dimethylamino)methyl)cyclohexanamine (310 mg, 2.0 mmol) to afford the product (350 mg, 93%) as a white solid: ESI MS m/z 375 [M+H]+.

Sources & evidence

ORD record
ord-67030fb3f4174311bda3939934a0d408
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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