Tetrafluoro-m-phenylenediamine dihydrochloride → 1-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one dihydrochloride

HRID 2365399Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]3=[O:25])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][CH2:29][C:3]1=2.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:49].Cl>>[ClH:49].[ClH:49].[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]3=[O:25])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:26][NH:27][CH2:28][CH2:29][C:3]1=2

Participants

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 67986818tert-Butyl 5-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 679694221-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one dihydrochlorideYield 94%

Procedure

tert-Butyl 5-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (180 mg, 0.368 mmol) was deprotected and converted to the dihydrochloride salt according to Example 2 (step g) to provide the title compound (134 mg, 94%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.59 (d, J=8.3 Hz, 1H), 7.46 (d, J=1.5 Hz, 1H), 7.40-7.33 (m, 4H), 7.32-7.28 (m, 1H), 7.08-7.07 (dd, J=8.3, 1.7 Hz, 1H), 4.45 (s, 2H), 4.28-4.16 (m, 2H), 4.16-4.01 (m, 2H), 3.95-3.76 (m, 2H), 3.72 (s, 3H), 3.63-3.55 (m, 4H), 3.27-3.16 (m, 2H), 3.13-3.08 (m, 2H); ESI MS m/z 389 [M+H]+; HPLC (Method B)>99% (AUC), tR=10.1 min.

Sources & evidence

ORD record: ord-78530462d58b47dab69b4bd304c73600
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697700B2

Reaction notes

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