Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178492959, compound

HRID 526142Notes

Reaction equation

HRID 526142 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]1.[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[C:31]([Cl:35])[C:32]=1[O:33][CH3:34].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[ClH:1].[ClH:26].[Cl:26][C:27]1[CH:28]=[C:29]([C:2]2[N:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]2)[CH:30]=[C:31]([Cl:35])[C:32]=1[O:33][CH3:34]

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 41973523,5-Dichloro-4-methoxyphenylboronic acidHCID 178467145HCID 178467145, compound

Product 1

HCID 178492959HCID 178492959, compoundYield 87,051.898%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]-cyclohexylamino}-1,5-naphthyridin-3-yl)ethanone (77 g, 0.21 mmol) was reacted with (3,5-dichloro-4-methoxyphenyl)boronic acid (70 g, 0.32 mmol) followed by formation of the dihydrochloride salt to afford the desired product (80 g, 66%) as a brown solid: 1H NMR (300 MHz, CD3OD) δ 9.18 (s, 1H), 8.52 (d, J=9.0 Hz, 1H), 8.39 (d, J=9.0 Hz, 1H), 8.20 (s, 2H), 5.74-5.59 (m, 1H), 3.99 (s, 3H), 3.09 (d, J=6.6 Hz, 2H), 2.94 (s, 6H), 2.76 (s, 3H), 2.48-2.40 (m, 2H), 2.10-2.00 (m, 3H), 1.79-1.61 (m, 2H), 1.50-1.31 (m, 2H); ESI MS m/z 501 [M+H]+; HPLC>99% (AUC), tR=10.49 min.

Sources & evidence

ORD record
ord-1b0c7002f2ce445b85e902a5a8e0f087
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

Loading…