1-(tert-Butoxycarbonyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole → HCID 178467127, compound

HRID 526214Notes

Reaction equation

HRID 526214 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.[CH3:26][C:27]1[C:31](B2OC(C)(C)C(C)(C)O2)=[C:30]([CH3:41])[N:29]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[N:28]=1>>[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:31]3[C:27]([CH3:26])=[N:28][N:29]([C:42]([O:44][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:43])[C:30]=3[CH3:41])=[N:3]2)=[N:8][CH:7]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 162183871-(tert-Butoxycarbonyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazoleHCID 178467145HCID 178467145, compound

Product 1

HCID 178467127HCID 178467127, compoundYield 76.8%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]-cyclohexylamino}-1,5-naphthyridin-3-yl)ethanone (92 mg, 0.25 mmol) was reacted with tert-butyl 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (120 mg, 0.37 mmol) to afford crude product (100 mg) as a brown solid which was carried forward without any purification: ESI MS m/z 521 [M+H]+

Sources & evidence

ORD record
ord-e42a0391eeaa4c0c9ae3f100e567cb8a
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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