Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 67969324, compound

HRID 2365397Notes

Reaction equation

HRID 2365397 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=4)[CH2:13][C:12]3=[O:27])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH2:31][C:3]1=2.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:51].Cl>>[ClH:51].[ClH:51].[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][N:18]=4)[CH2:13][C:12]3=[O:27])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][C:3]1=2

Participants

3

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86667073HCID 86667073, compound

Product 1

HCID 67969324HCID 67969324, compoundYield 46%

Procedure

tert-Butyl 5-methyl-7-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (72 mg, 0.14 mmol) was deprotected and converted to the dihydrochloride salt according to Example 2 (step g) to provide the title compound (32 mg, 46%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 9.15 (s, 2H), 8.49 (s, 1H), 7.90-7.88 (dd, J=9.1, 2.5 Hz, 1H), 7.49 (d, J=6.6 Hz, 1H), 7.48 (s, 1H), 7.04-7.00 (dd, J=8.4, 1.7 Hz, 1H), 7.01 (d, J=9.0 Hz, 1H), 4.39 (s, 2H), 4.35-4.30 (m, 2H), 4.08-4.04 (m, 2H), 3.91-3.88 (m, 2H), 3.65 (s, 3H), 3.54-3.40 (m, 3H), 3.09-3.04 (m, 2H); ESI MS m/z 430 [M+H]+; HPLC (Method B) 99% (AUC), tR=14.4 min.

Sources & evidence

ORD record
ord-87c1d560798c4081abe27dfd8e09b82f
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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