Ammonia → (S)-3-(Methylsulfonamido)-5-(4-((1-(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)phenyl methanesulfonate

HRID 1052808Notes

Reaction equation

HRID 1052808 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=[CH:37][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:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:7]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O.N>>[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=[CH:37][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:9]=[C:8]([NH:48][S:49]([CH3:52])(=[O:50])=[O:51])[CH:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131736165(S)-3-(Methylsulfonamido)-5-(4-((1-(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

Product 1

HCID 118433771(S)-3-(Methylsulfonamido)-5-(4-((1-(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)phenyl methanesulfonateYield 52%

Procedure

(S)-3-(Methylsulfonamido)-5-(4-((1-(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 (82 mg, 0.07 mmol) was treated with trifluoroacetic acid (3 ml, 39 mmol) and a solution of ammonia (7N in methanol, 2.5 ml, 18 mmol) according to the method described in Example 27 to give 23 mg (52% yield) of the title compound. Purity 99%.

Sources & evidence

ORD record
ord-0c644229e76d4593a77ee4baba1d8e04
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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