2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178467090, compound

HRID 526125Notes

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][CH:16]1[CH2:21][CH2:20][CH:19]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[CH2:18][CH2:17]1.[Cl:30][C:31]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[C:33]([Cl:46])[C:32]=1[OH:47]>>[ClH:1].[ClH:30].[ClH:1].[Cl:46][C:33]1[CH:34]=[C:35]([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]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]3)[CH2:20][CH2:21]2)[CH:36]=[C:31]([Cl:30])[C:32]=1[OH:47]

Participants

Reactant 2

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

HCID 117773167HCID 117773167, compound

Product 1

HCID 178467090HCID 178467090, compoundYield 125.1%

Procedure

Following general procedure II, 1-(6-chloro-4-{4-[(4-methylpiperazin-1-yl)methyl]-cyclohexyl amino}-1,5-naphthyridin-3-yl)ethanone (32 mg, 0.076 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (26 mg, 0.092 mmol) followed by formation of the trihydrochloride salt to afford the desired product (31 mg, 67%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.46 (d, J=8.9 Hz, 1H), 8.33 (d, J=8.9 Hz, 1H), 8.10 (s, 2H), 5.73-5.68 (m, 1H), 3.75 (br s, 8H), 3.16 (br s, 2H), 3.02 (s, 3H), 2.76 (s, 3H), 2.46-2.42 (m, 2H), 2.22-2.14 (m, 2H), 2.10-2.00 (m, 1H), 1.72-1.63 (m, 2H), 1.46-1.37 (m, 2H); ESI MS m/z 542 [M+H]+; HPLC 96.7% (AUC), tR=9.37 min.

Sources & evidence

ORD record: ord-4c35d397e27c4efabcf3d123fe744188
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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