5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → Tert-butyl 4-(5-(1-oxoisoindolin-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)piperidine-1-carboxylate

HRID 1093962Notes

Reaction equation

HRID 1093962 reaction equation
Br[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[C:38](=[O:42])[NH:37][CH2:36]3)O1>>[O:42]=[C:38]1[C:39]2[C:35](=[CH:34][C:33]([C:2]3[N:7]4[N:8]=[CH:9][N:10]=[C:6]4[C:5]([NH:11][CH:12]4[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]4)=[N:4][CH:3]=3)=[CH:41][CH:40]=2)[CH2:36][NH:37]1

Participants

3

Reactant 2

HCID 219557955-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 57699494Tert-butyl 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)piperidine-1-carboxylate

Product 1

HCID 25115608Tert-butyl 4-(5-(1-oxoisoindolin-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)piperidine-1-carboxylate

Procedure

Prepared from the product of Step 1 and Intermediate 4 (5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one) using the procedure described in Example 1, Step 2. 1H-NMR (400 MHz, d6-DMSO) =1.45 (s, 9H), 1.61-1.65 (m, 2H), 1.88-1.95 (m, 2H), 2.82-2.99 (brm, 2H), 3.99-4.04 (m, 2H), 4.27-4.38 (brm, 1H), 4.50 (s, 2H), 7.81 (d, 1H, J=8), 7.92 (s, 1H), 8.03-8.11 (m, 2H), 8.18 (s, 1H), 8.63 (s, 1H), 8.67 (s, 1H). LCMS: Rt 3.07 min (98.3%), m/z (APCI) 450 (M+H)+.

Sources & evidence

ORD record
ord-bb0344f7d7fe482a8e86b34461bd3ca3
Source dataset
uspto-grants-2012_03
Patent number
US08133895B2

Reaction notes

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