N'-[4-(6-methoxy-4-piperazin-1-yl-2-naphthyl)pyrimidin-2-yl]-N,N-dimethylpropane-1,3-diamine → N1-(4-(4-(4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-6-methoxynaphthalen-2-yl)pyrimidin-2-yl)-N3,N3-dimethylpropane-1,3-diamine

HRID 1921990Notes

Reaction equation

HRID 1921990 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[N:14]=1)[CH:7]=[C:6]2[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[Br:32][C:33]1[C:41]2[C:36](=[N:37][CH:38]=[N:39][C:40]=2Cl)[NH:35][N:34]=1>>[Br:32][C:33]1[C:41]2[C:36](=[N:37][CH:38]=[N:39][C:40]=2[N:29]2[CH2:28][CH2:27][N:26]([C:6]3[C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=[C:8]([C:13]4[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[N:14]=4)[CH:7]=3)[CH2:31][CH2:30]2)[NH:35][N:34]=1

Participants

3

Reactant 2

HCID 53257826N'-[4-(6-methoxy-4-piperazin-1-yl-2-naphthyl)pyrimidin-2-yl]-N,N-dimethylpropane-1,3-diamineHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178487401N1-(4-(4-(4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-6-methoxynaphthalen-2-yl)pyrimidin-2-yl)-N3,N3-dimethylpropane-1,3-diamine

Procedure

N1-(4-(4-(4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-6-methoxynaphthalen-2-yl)pyrimidin-2-yl)-N3,N3-dimethylpropane-1,3-diamine was synthesized according to General Procedure E except N′-[4-(6-methoxy-4-piperazin-1-yl-2-naphthyl)pyrimidin-2-yl]-N,N-dimethylpropane-1,3-diamine and 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine were used. N1-(4-(4-(4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-6-methoxynaphthalen-2-yl)pyrimidin-2-yl)-N3,N3-dimethylpropane-1,3-diamine 178 was isolated as a solid. M.p.=152-155° C. LC/MS (m/z/): 618 [M+H].

Workup

  1. customN1-(4-(4-(4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-6-methoxynaphthalen-2-yl)pyrimidin-2-yl)-N3,N3-dimethylpropane-1,3-diamine was synthesized

Sources & evidence

ORD record
ord-3ed385d6a16c495a8e411c9eaf4da63a
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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