3-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-one → 3-(1-(4-amino-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one

HRID 634479Notes

Reaction equation

HRID 634479 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:11]2[C:6](=[N:7][CH:8]=[N:9][C:10]=2[NH2:12])[NH:5][N:4]=1.Br[CH:16]([C:18]1[O:19][C:20](=[O:34])[C:21]2[C:26]([C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:17]>>[NH2:12][C:10]1[N:9]=[CH:8][N:7]=[C:6]2[N:5]([CH:16]([C:18]3[O:19][C:20](=[O:34])[C:21]4[C:26]([C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH3:17])[N:4]=[C:3]([C:2]([F:13])([F:1])[F:14])[C:11]=12

Participants

3

Reactant 2

HCID 1181310753-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-one2×HCID 178508724HCID 178508724, compound

Product 1

HCID 1181313903-(1-(4-amino-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-oneYield 15%

Procedure

The title compound was made in a similar way as that of the compound of example 1 using 3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G16, 45 mg, 0.222 mmol) 3-(1-bromoethyl)-4-phenyl-1H-isochromen-1-one (intermediate C7, 72.9 mg, 0.222 mmol). to give the title compound (15 mg, 0.033 mmol, 15.0% yield) as white solid.

Sources & evidence

ORD record
ord-aeafde1fee014914a064130f75581d79
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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