Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178467094, compound

HRID 2178803Notes

Reaction equation

HRID 2178803 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:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[ClH:1].[ClH:26].[Cl:26][C:27]1[CH:32]=[C:31]([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[CH2:17][CH2:18][C@H:19]([CH2:22][N:23]([CH3:24])[CH3:25])[CH2:20][CH2:21]2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43]

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178467145HCID 178467145, compound

Product 1

HCID 178467094HCID 178467094, compoundYield 64.2%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclohexyl amino}-1,5-naphthyridin-3-yl)ethanone (20 mg, 0.055 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (29 mg, 0.10 mmol) followed by formation of the dihydrochloride salt to afford the desired product (18 mg, 58%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.46 (d, J=9.1 Hz, 1H), 8.33 (d, J=9.1 Hz, 1H), 8.12 (s, 2H), 5.75-5.67 (m, 1H), 3.09 (d, J=6.6 Hz, 2H), 2.94 (s, 6H), 2.76 (s, 3H), 2.48-2.41 (m, 2H), 2.09-1.98 (m, 1H), 1.75-1.63 (m, 1H), 1.48-1.36 (m, 2H). ESI MS m/z 487 [M+H]+; HPLC>99% (AUC), tR=9.67 min.

Sources & evidence

ORD record
ord-dcf9b4a97bab4f8596e18d4d0bbe89d4
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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