Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 68657703, compound

HRID 930691Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[N:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:24])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:25][NH:26][CH2:27][CH2:28][C:3]1=2.[C:29]1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:41].Cl>>[ClH:41].[ClH:41].[CH3:29][N:26]1[CH2:27][CH2:28][C:3]2[N:2]([CH3:1])[C:10]3[CH:9]=[C:8]([N:11]4[CH:16]=[CH:15][C:14]([C:17]5[N:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=5)=[CH:13][C:12]4=[O:24])[CH:7]=[CH:6][C:5]=3[C:4]=2[CH2:25]1

Participants

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 57950251HCID 57950251, compound

Product 1

HCID 68657703HCID 68657703, compoundYield 74%

Procedure

1-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-(6-methylpyridazin-3-yl)pyridin-2(1H)-one (77 mg, 0.21 mmol) was reacted according to the procedure of Example 47 to provide the free-base. Conversion to the dihydrochloride salt using the procedure of Example 30 (step g) provided the title compound (60 mg, 74%) as a yellow solid: mp 285-288° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.9 (s, 1H), 8.32 (d, J=8.8 Hz, 1H), 7.85 (d, J=7.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.64 (d, J=1.5 Hz, 1H), 7.56 (d, J=8.3 Hz, 1H), 7.25 (d, J=1.7 Hz, 1H), 7.14-7.11 (m, 2H), 4.65 (d, J=12.1 Hz, 1H), 4.31 (dd, J=14.2, 7.5 Hz, 1H), 3.81-3.74 (m, 1H), 3.71 (s, 3H), 3.55-3.45 (m, 1H), 3.26-3.15 (m, 2H), 2.98 (s, 3H), 2.72 (s, 3H); ESI MS m/z 386 [M+H]+; HPLC (Method B)>99% (AUC), tR=9.4 min.

Workup

customto provide the free-base

Sources & evidence

ORD record: ord-2e855ca99f4f40a187b65446b6af03bd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296743B2

Reaction notes

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