Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 68657502, compound

HRID 1020593Notes

Reaction equation

HRID 1020593 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH: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.[C:30]1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:42].Cl>>[ClH:42].[ClH:42].[CH3:30][N:27]1[CH2:28][CH2:29][C:3]2[N:2]([CH3:1])[C:10]3[CH:9]=[C:8]([N:11]4[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=5)=[CH:13][C:12]4=[O:25])[CH:7]=[CH:6][C:5]=3[C:4]=2[CH2:26]1

Participants

3

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 44193893HCID 44193893, compound

Product 1

HCID 68657502HCID 68657502, compoundYield 98%

Procedure

1-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-(pyridin-2-ylmethoxy)pyridin-2(1H)-one (45 mg, 0.116 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 (54 mg, 98%) as a white solid: mp 260-265° C.; 1H NMR (500 MHz, CD3OD) δ 8.87 (d, J=5.7 Hz, 1H), 8.58 (overlapping dd, J=8.2 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.00 (overlapping dd, J=6.6 Hz, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.59 (d, J=8.3 Hz, 1H), 7.49 (s, 1H), 7.07 (dd, J=8.3, 1.7 Hz, 1H), 6.44 (dd, J=7.5, 2.6 Hz, 1H), 6.20 (d, J=2.0 Hz, 1H), 5.56 (s, 2H), 4.76 (d, J=14.2 Hz, 1H), 4.40 (d, J=14.2 Hz, 1H), 3.91 (m, 1H), 3.74 (s, 3H), 3.61 (m, 1H), 3.29-3.17 (m overlapping with solvent, 2H), 3.13 (s, 3H); ESI MS m/z 401 [M+H]+; HPLC (Method B)>99% (AUC), tR=9.2 min.

Workup

  1. customto provide the free-base

Sources & evidence

ORD record
ord-de4a6494ef364617a44d0d80927873fe
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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