tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate → HCID 178467130, compound

HRID 526109Notes

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]([CH3:25])[CH3:24])[CH2:18][CH2:17]1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][N:37](C(OC(C)(C)C)=O)[CH:38]=2)O1>>[ClH:1].[ClH:1].[ClH: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:34]4[CH:35]=[N:36][NH:37][CH:38]=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

Reactant 2

HCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

HCID 71667497C19H25ClN4O

Product 1

HCID 178467130HCID 178467130, compoundYield 127.5%

Procedure

Following general procedure II, 1-(6-chloro-4-{4-[(dimethylamino)methyl]-cyclohexylamino}-1,5-naphthyridin-3-yl)ethanone (55 mg, 0.15 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (66 mg, 0.225 mmol) followed by formation of the trihydrochloride salt to afford the desired product (32 mg, 42%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.10 (s, 1H), 8.34 (s, 2H) 8.30-8.23 (m, 2H), 5.64 (m, 1H), 3.14 (d, J=6.7 Hz, 2H), 2.94 (s, 6H), 2.75 (s, 3H), 2.47 (d, J=13.0 Hz, 2H), 2.09-1.97 (m, 3H), 1.73-1.61 (m, 2H), 1.45-1.33 (m, 2H); ESI MS m/z 393 [M+H]+; HPLC 98.3% (AUC), tR=8.60 min.

Sources & evidence

ORD record: ord-a99da7718485474fad5ca6a3612ec661
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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