Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 44194186, compound

HRID 930700Notes

Reaction equation

HRID 930700 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[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=4)=[CH: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.[C:32]1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[CH3:32][N:29]1[CH2:30][CH2:31][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[CH:18]=[N:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=5)=[CH:13][C:12]4=[O:27])[CH:7]=[CH:6][C:5]=3[C:4]=2[CH2:28]1

Participants

3

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 44194091HCID 44194091, compound

Product 1

HCID 44194186HCID 44194186, compoundYield 29%

Procedure

1-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one (77 mg, 0.18 mmol) was reacted according to the procedure of Example 47 and converted to the dihydrochloride to provide the title compound (27 mg, 29%) as a yellow solid: mp 295-300° C.; 1H NMR (500 MHz, CD3OD) δ 9.09 (d, J=1.7 Hz, 1H), 8.42 (dd, J=8.1, 2.0 Hz, 1H), 7.97 (d, J=8.2 Hz, 1H), 7.85 (d, J=7.1 Hz, 1H), 7.62 (d, J=8.3 Hz, 1H), 7.58 (d, J=1.5 Hz, 1H), 7.15 (dd, J=8.3, 1.8 Hz, 1H), 7.02 (d, J=1.8 Hz, 1H), 6.89 (dd, J=7.1, 2.0 Hz, 1H), 4.79-4.37 (br m, 2H), 3.90-3.60 (br m, 5H), 3.30 (br m, 2H), 3.14 (s, 3H); ESI MS m/z 439 [M+H]+; HPLC (Method B)>99% (AUC), tR=12.4 min.

Sources & evidence

ORD record
ord-94a7509e05ba40108474c4574db7dfd3
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

Loading…