2-Cyanopyrimidine-5-boronic acid pinacol ester → HCID 178467129, compound

HRID 526121Notes

Reaction equation

Cl[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.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][C:37]([C:40]#[N:41])=[N:38][CH:39]=2)O1>>[C:12]([C:6]1[C:5]([NH:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]2)=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([C:34]3[CH:35]=[N:36][C:37]([C:40]#[N:41])=[N:38][CH:39]=3)=[N:3]2)=[N:8][CH:7]=1)(=[O:14])[CH3:13]

Participants

Reactant 2

HCID 164142762-Cyanopyrimidine-5-boronic acid pinacol ester

HCID 178467145HCID 178467145, compound

Product 1

HCID 178467129HCID 178467129, compoundYield 23.3%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclo-hexylamino}-1,5-naphthyridin-3-yl)ethanone (87 mg, 0.24 mmol) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carbonitrile (83 mg, 0.36 mmol) to afford the desired product (24 mg, 23%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.62 (s, 2H), 9.23 (s, 1H), 8.68 (d, J=8.9 Hz, 1H), 8.51 (d, J=8.9 Hz, 1H), 5.52-5.41 (m, 1H), 3.12 (d, J=6.8 Hz, 2H), 2.94 (s, 6H), 2.77 (s, 3H), 2.51-2.42 (m, 2H), 2.08-1.94 (m, 3H), 1.88-1.65 (m, 2H), 1.37-1.25 (m, 2H); ESI MS m/z 430 [M+H]+; HPLC>99% (AUC), tR=8.73 min.

Sources & evidence

ORD record: ord-90d2882ce8fa41b59bdb63ed802ea947
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

Loading…