Ammonia → (S)-3-(4-((1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)phenyl methanesulfonate
Reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([C:12]2[C:20]3[C:19]([NH:21][C@H:22]([C:24]4[N:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:28](=[O:36])[C:27]5=[C:37]([CH3:40])[CH:38]=[CH:39][N:26]5[N:25]=4)[CH3:23])=[N:18][CH:17]=[N:16][C:15]=3[N:14](COCC[Si](C)(C)C)[CH:13]=2)[CH:9]=[C:8]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:7]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O.N>>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[C:8]([NH:49][S:50]([CH3:53])(=[O:51])=[O:52])[CH:9]=[C:10]([C:12]2[C:20]3[C:19]([NH:21][C@H:22]([C:24]4[N:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:28](=[O:36])[C:27]5=[C:37]([CH3:40])[CH:38]=[CH:39][N:26]5[N:25]=4)[CH3:23])=[N:18][CH:17]=[N:16][C:15]=3[NH:14][CH:13]=2)[CH:11]=1)(=[O:3])=[O:4]Participants
4
Reactant 3
Product 1
Procedure
(S)-3-(Methylsulfonamido)-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl methanesulfonate (169 mg, 0.19 mmol) was treated with trifluoroacetic acid (4.7 ml, 61 mmol) and a solution of ammonia (7N in methanol, 4.0 ml, 17 mmol) according to the method described in Example 27 to give 102 mg (83% yield) of the title compound. Purity 99%.
Sources & evidence
- ORD record
- ord-ddc357ae9aa14196aac3efcac4dbfda1
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388189B2
Reaction notes
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