Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 136927300, compound

HRID 526097Notes

Reaction equation

HRID 526097 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][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1.[Cl:24][C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[C:27]([Cl:40])[C:26]=1[OH:41].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[ClH:1].[ClH:24].[Cl:24][C:25]1[CH:30]=[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][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)[CH:28]=[C:27]([Cl:40])[C:26]=1[OH:41]

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 117774185HCID 117774185, compound

Product 1

HCID 136927300HCID 136927300, compoundYield 10.2%

Procedure

Following general procedure II, 1-{6-chloro-4-[(1-methylpiperidin-4-yl)methylamino]-1,5-naphthyridin-3-yl}ethanone (60 mg, 0.18 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (78 mg, 0.27 mmol) followed by formation of the dihydrochloride salt to afford the desired product (7.3 mg, 7.6%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.18 (s, 1H), 8.48 (d, J=9.0 Hz, 1H), 8.35 (d, J=8.9 Hz, 1H), 8.11 (s, 2H), 4.60 (d, J=7.1 Hz, 2H), 3.65-3.59 (m, 2H), 3.09 (td, J=13.0, 2.8 Hz, 2H), 2.88 (s, 3H), 2.77 (s, 3H), 2.34 (br s, 1H), 2.27 (d, J=14.7 Hz, 2H), 1.80-1.67 (m, 2H); ESI MS m/z 459 [M+H]+; HPLC>99% (AUC), tR=9.39 min.

Sources & evidence

ORD record
ord-e19100f722b94b69a22b13e1b6e7fab6
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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