Trifluoroacetic acid → 2,2,2-trifluoro-1-{6-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-1H-indol-3-yl}-ethanone

HRID 2273023Notes

Reaction equation

HRID 2273023 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8]3[N:9]([N:13]=[C:14]([NH2:16])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1.Br[C:18]1[CH:26]=[C:25]2[C:21]([C:22]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][NH:24]2)=[CH:20][CH:19]=1.BrC1C=C2C(C=CN2)=CC=1.C(O)(C(F)(F)F)=O>CN(C=O)C>[F:31][C:28]([F:29])([F:30])[C:27]([C:22]1[C:21]2[C:25](=[CH:26][C:18]([NH:16][C:14]3[N:15]=[C:8]4[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)=[N:12][CH:11]=[CH:10][N:9]4[N:13]=3)=[CH:19][CH:20]=2)[NH:24][CH:23]=1)=[O:32]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 6764936-BromoindoleHCID 127063701-(6-bromo-1H-indol-3-yl)-2,2,2-trifluoroethanoneHCID 665833238-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine

Product 1

HCID 897690672,2,2-trifluoro-1-{6-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-1H-indol-3-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine is reacted with 1-(6-bromo-1H-indol-3-yl)-2,2,2-trifluoro-ethanone, available by reaction of 6-bromo-1H-indole (1 eq.) with TFA (1.6 eq) in DMF at 120° C. for 1 h, under conditions described in general procedure 2.

Sources & evidence

ORD record
ord-06106bba795a427e968dd324c580e0b4
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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