HCID 53257946, compound → HCID 178490141, compound

HRID 1921992Notes

Reaction equation

HRID 1921992 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:27]=[C:26]([N:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:34][CH3:35])[CH:24]=4)[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH:6]=[CH:7][CH:8]=1.[Br:36][C:37]1[C:45]2[C:40](=[N:41][CH:42]=[N:43][C:44]=2Cl)[NH:39][N:38]=1>>[Br:36][C:37]1[C:45]2[C:40](=[N:41][CH:42]=[N:43][C:44]=2[N:31]2[CH2:30][CH2:29][N:28]([C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:34][CH3:35])[CH:24]=4)[CH:19]=[C:18]([C:16]4[CH:15]=[CH:14][N:13]=[C:12]([NH:11][CH2:10][CH2:9][C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=5)[N:17]=4)[CH:27]=3)[CH2:33][CH2:32]2)[NH:39][N:38]=1

Participants

3

Reactant 2

HCID 53257946HCID 53257946, compoundHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178490141HCID 178490141, compound

Procedure

4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-2-amine was synthesized according to General Procedure E except N-[2-(3-methoxyphenyl)ethyl]-4-(6-methoxy-4-piperazin-1-yl-2-naphthyl)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-[2-(3-methoxyphenyl)ethyl]pyrimidin-2-amine 180 was isolated as a pale yellow solid. M.p.=200-203° C. 400 MHz 1H NMR (DMSO-d6) δ: 12.8 (br s, 1H), 8.36 (m, 3H), 8.04 (s, 1H), 7.94 (d, J=9 Hz, 1H), 7.74 (s, 1H), 7.24 (m, 3H), 6.91 (m, 2H), 6.72 (d, J=9.4 Hz, 1H), 6.19 (m, 1H), 4.25 (m, 4H), 4.01 (s, 3H), 3.81-3.76 (m, 5H), 3.41-3.39 (m, 4H), 3.00 (t, J=7.3 Hz, 2H); Experimental Elemental Analysis (0.26 equivalents of water)=59.04% C, 4.83% H, 18.00% N; Calculated Elemental Analysis 59.05% C, 4.88% H, 18.78% N; LCMS (m/z): 667 [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-[2-(3-methoxyphenyl)ethyl]pyrimidin-2-amine was synthesized

Sources & evidence

ORD record
ord-0579d914667d4f089167756b88e66af1
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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