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

HRID 2365409Notes

Reaction equation

[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[C:18]5[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][C:19]=5[N:20]([CH3:23])[C:21]=4[CH:22]=3)[C:10](=[O:35])[CH2:9]2)=[CH:4][CH:3]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:50].Cl>>[ClH:50].[ClH:50].[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[C:18]5[CH2:27][NH:26][CH2:25][CH2:24][C:19]=5[N:20]([CH3:23])[C:21]=4[CH:22]=3)[C:10](=[O:35])[CH2:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 67986820tert-Butyl 7-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 679692524-(4-Fluorophenethyl)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)piperazin-2-one dihydrochlorideYield 63%

Procedure

tert-Butyl 7-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (730 mg, 1.44 mmol) was deprotected and converted to the dihydrochloride according to Example 2 (step g) to provide the title compound (433 mg, 63%) as a white solid: 298° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 12.32 (s, 1H), 9.53 (s, 2H), 7.53 (d, J=8.3 Hz, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.39-7.34 (m, 2H), 7.20 (t, J=8.8 Hz, 2H), 7.02-7.00 (dd, J=8.3, 1.6 Hz, 1H), 4.38 (s, 2H), 4.27-4.19 (m, 1H), 4.19-3.99 (m, 2H), 3.94-3.81 (m, 2H), 3.66 (s, 3H), 3.64-3.54 (m, 1H), 3.54-3.33 (m, 4H), 3.19-3.11 (m, 2H), 3.10-3.05 (m, 2H); ESI MS m/z 407 [M+H]+; HPLC (Method B)>99% (AUC), tR=11.9 min.

Sources & evidence

ORD record: ord-fd51170a086649d8a3910e1e8f912180
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697700B2

Reaction notes

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