2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 136266715, compound

HRID 526105Notes

Reaction equation

HRID 526105 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:22])[CH3:21])=[C:13]3[NH:23][C:24]2[CH:25]=[N:26][C:27]([NH:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:28][CH:29]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].[Cl:36]C1C=C(B2OC(C)(C)C(C)(C)O2)C=C(Cl)C=1O>>[ClH:1].[ClH:36].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:22])[CH3:21])=[C:13]3[NH:23][C:24]2[CH:25]=[N:26][C:27]([NH:30][CH2:31][CH2:32][N:33]([CH3:34])[CH3:35])=[CH:28][CH:29]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8]

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 136266716HCID 136266716, compound

Product 1

HCID 136266715HCID 136266715, compoundYield 233.6%

Procedure

Following general procedure II, 1-[6-(3,5-dichloro-4-hydroxyphenyl)-4-{6-[2-(dimethylamino)ethylamino ]pyridin-3-ylamino}-1,5-naphthyridin-3-yl]ethanone (69 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 trihydrochloride salt to afford the desired product (87 mg, 78%) as a yellow-orange solid: 1H NMR (500 MHz, D2O) δ 9.22 (s, 1H), 8.22 (d, J=8.9 Hz, 1H), 8.02 (d, J=9.1 Hz, 1H), 7.92 (d, J=2.5 Hz, 1H), 7.59-7.53 (m, 1H), 6.98 (s, 2H), 6.79 (d, J=9.4 Hz, 1H), 3.67 (t, J=6.4 Hz, 2H), 3.23 (t, J=6.4 Hz, 2H), 2.82 (s, 6H), 2.80 (s, 3H); ESI MS m/z 511 [M+H]+; HPLC>99% (AUC), tR=9.13 min.

Sources & evidence

ORD record
ord-6869210027a347ea8e1d849e9b0c9cab
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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