2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178467076, compound

HRID 526122Notes

Reaction equation

HRID 526122 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.[CH3:26][C:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([CH3:42])[C:28]=1[OH:43]>>[Cl-:1].[Cl-:1].[CH3:24][N:23]([CH2:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([NH:15][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:31]4[CH:30]=[C:29]([CH3:42])[C:28]([OH:43])=[C:27]([CH3:26])[CH:32]=4)[N:3]=3)[N:8]=[CH:7][C:6]=2[C:12](=[O:14])[CH3:13])[CH2:17][CH2:18]1)[CH3:25]

Participants

3

Reactant 2

HCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178467145HCID 178467145, compound

Product 1

HCID 178467076HCID 178467076, compoundYield 95.5%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclo-hexylamino}-1,5-naphthyridin-3-yl)ethanone (60 mg, 0.166 mmol) was reacted with 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (62 mg, 0.25 mmol) followed by formation of the trihydrochloride salt to afford the desired product (41 mg, 48%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.10 (s, 1H), 8.39 (d, J=9.0 Hz, 1H), 8.26 (d, J=9.0 Hz, 1H), 7.72 (s, 2H), 5.82-5.73 (m, 1H), 3.06 (d, J=6.6 Hz, 2H), 2.93 (s, 6H), 2.75 (s, 3H), 2.49-2.42 (m, 2H), 2.35 (s, 6H), 2.09-1.98 (m, 3H), 1.73-1.60 (m, 2H), 1.40-1.27 (m, 2H); ESI MS m/z 447 [M+H]+; HPLC 98.4% (AUC), tR=9.81 min.

Sources & evidence

ORD record
ord-c93177d187004ea5b2424ba25a9b9b19
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

Loading…