N,N-Dimethyl-1,3-propanediamine → N'-[3-({7-methoxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)propyl]-N,N-dimethylpropane-1,3-diamine

HRID 1921996Notes

Reaction equation

HRID 1921996 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH:9]=[C:8]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=2)[CH:7]=1.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30][NH2:31]>>[CH3:17][O:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=3)[CH:7]=[C:6]2[NH:5][CH2:4][CH2:3][CH2:2][NH:31][CH2:30][CH2:29][CH2:28][N:27]([CH3:32])[CH3:26])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 532581654-(4-((3-bromopropyl)amino)-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine

Product 1

HCID 67305338N'-[3-({7-methoxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)propyl]-N,N-dimethylpropane-1,3-diamine

Procedure

N′-[3-({7-methoxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)propyl]-N,N-dimethylpropane-1,3-diamine 189 was synthesized according to General Procedure H except in Step 2 4-(4-((3-bromopropyl)amino)-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine and N1,N1-dimethylpropane-1,3-diamine were used. N′-[3-({7-methoxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)propyl]-N,N-dimethylpropane-1,3-diamine 191 was isolated as a red-orange solid. M.p.=142-144° C. LCMS (m/z): 423 [M+H].

Workup

  1. customN′-[3-({7-methoxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)propyl]-N,N-dimethylpropane-1,3-diamine 189 was synthesized

Sources & evidence

ORD record
ord-9588e11a717f4362979ac7d4f838b165
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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