5-Bromo-3,3-dimethyl-isoindolin-1-one → 5-{8-[4-(4-Isopropylpiperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-3,3-dimethyl-2,3-dihydroisoindol-1-one

HRID 605984Notes

Reaction equation

HRID 605984 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2([CH3:13])[CH3:12].B([O-])[O-].Br[C:18]1[N:23]2[N:24]=[CH:25][N:26]=[C:22]2[C:21]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][N:37]([CH:40]([CH3:42])[CH3:41])[CH2:36][CH2:35]3)=[CH:30][CH:29]=2)=[N:20][CH:19]=1>>[CH:40]([N:37]1[CH2:36][CH2:35][N:34]([C:31]2[CH:30]=[CH:29][C:28]([NH:27][C:21]3[C:22]4[N:23]([N:24]=[CH:25][N:26]=4)[C:18]([C:2]4[CH:3]=[C:4]5[C:8](=[CH:9][CH:10]=4)[C:7](=[O:11])[NH:6][C:5]5([CH3:13])[CH3:12])=[CH:19][N:20]=3)=[CH:33][CH:32]=2)[CH2:39][CH2:38]1)([CH3:42])[CH3:41]

Participants

4

Reactant 3

HCID 575899965-Bromo-3,3-dimethyl-isoindolin-1-oneHCID 57590046(5-Bromo[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-isopropylpiperazin-1-yl)-phenyl]amineHCID 178514824HCID 178514824, compound

Product 1

HCID 248896265-{8-[4-(4-Isopropylpiperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-3,3-dimethyl-2,3-dihydroisoindol-1-one

Procedure

5-Bromo-3,3-dimethyl-2,3-dihydroisoindol-1-one is converted to the corresponding boronate in a fashion analogous to Intermediate 6, Step 3. This is then used to prepare the title compound from (5-bromo[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-isopropylpiperazin-1-yl)-phenyl]amine using methods as described for Compound 120, Step 4. LCMS: Rt=0.92 (100%), m/z=497 (M+H)+.

Sources & evidence

ORD record
ord-c995c573126f435fb5271030589264da
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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