Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178484102, compound

HRID 526088Notes

Reaction equation

HRID 526088 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]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([N:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]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[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([NH:16][C@H:17]4[CH2:18][CH2:19][C@H:20]([N:23]([CH3:25])[CH3:24])[CH2:21][CH2:22]4)[C:6]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:7][N:8]=3)[N:3]=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 178484104HCID 178484104, compound

Product 1

HCID 178484102HCID 178484102, compoundYield 103%

Procedure

Following general procedure II, trans-N1-[6-chloro-3-(methylsulfonyl)-1,5-naphthyridin-4-yl]-N4,N4-dimethylcyclohexane-1,4-diamine (40 mg, 0.10 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (43 mg, 0.15 mmol) followed by formation of the dihydrochloride salt to afford the desired product (45 mg, 75%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.93 (s, 1H), 8.51 (d, J=8.9 Hz, 1H), 8.37 (d, J=8.9 Hz, 1H), 8.12 (s, 2H), 5.65-5.55 (m, 1H), 3.50-3.41 (m, 1H), 3.39 (s, 3H), 2.91 (s, 6H), 2.67-2.57 (m, 2H), 2.33-2.27 (m, 2H), 1.87-1.73 (m, 4H). ESI MS m/z 509 [M+H]+; HPLC 98.0% (AUC), tR=9.95 min.

Sources & evidence

ORD record
ord-9d5b263839754161813c180c4b5bbe69
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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