HCID 67305125, compound → HCID 178495266, compound

HRID 1921989Notes

Reaction equation

HRID 1921989 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][O:23][CH3:24])[N:14]=1)[CH:7]=[C:6]2[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[Br:31][C:32]1[C:40]2[C:35](=[N:36][CH:37]=[N:38][C:39]=2Cl)[NH:34][N:33]=1>>[Br:31][C:32]1[C:40]2[C:35](=[N:36][CH:37]=[N:38][C:39]=2[N:28]2[CH2:27][CH2:26][N:25]([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][O:23][CH3:24])[N:14]=4)[CH:7]=3)[CH2:30][CH2:29]2)[NH:34][N:33]=1

Participants

3

Reactant 2

HCID 67305125HCID 67305125, compoundHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178495266HCID 178495266, compound

Procedure

4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-(3-methoxypropyl)pyrimidin-2-amine was synthesized according to General Procedure E except 4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)-N-(3-methoxypropyl)pyrimidin-2-amine and 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine were used. 4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-(3-methoxypropyl)pyrimidin-2-amine (177) was isolated as a yellow solid. M.p.=225-227° C. LCMS (m/z): 605 [M+H].

Workup

  1. custom4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-(3-methoxypropyl)pyrimidin-2-amine was synthesized

Sources & evidence

ORD record
ord-6ef76c70dc1d488e92780e93c2c1eb35
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

Loading…