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

HRID 2365401Notes

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][N: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][N: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 67986819tert-Butyl 5-methyl-7-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 679692151-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-(2-(pyridin-2-yl)ethyl)piperazin-2-one dihydrochlorideYield 10%

Procedure

tert-Butyl 5-methyl-7-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (210 mg, 0.429 mmol) was deprotected and converted to the dihydrochloride salt according to Example 2 (step g) to provide the title compound (19 mg, 10%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 12.90-11.93 (br s, 1H), 9.49 (s, 2H), 8.69 (d, J=3.9 Hz, 1H), 8.15-8.06 (m, 1H), 7.71-7.65 (m, 1H), 7.61-7.55 (m, 1H), 7.52 (d, J=8.3 Hz, 1H), 7.42 (d, J=1.5 Hz, 1H), 7.02-7.00 (dd, J=8.4, 1.6 Hz, 1H), 4.30 (s, 2H), 4.05 (s, 2H), 4.04-3.99 (m, 2H), 3.78-3.72 (m, 2H), 3.72-3.62 (m, 5H), 3.53-3.42 (m, 4H), 3.10-3.04 (m, 2H); ESI MS m/z 390 [M+H]+; HPLC (Method B) 97.7% (AUC), tR=11.6 min.

Sources & evidence

ORD record: ord-d9143f47c1f9447fa6487a9a7e6422c9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697700B2

Reaction notes

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