Ammonia → (S)-N-(2-Methoxy-5-(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)pyridin-3-yl)methanesulfonamide

HRID 1052691Notes

Reaction equation

HRID 1052691 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][C:6]([C:14]2[C:22]3[C:21]([NH:23][C@H:24]([C:26]4[N:31]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:30](=[O:38])[C:29]5=[C:39]([CH3:42])[CH:40]=[CH:41][N:28]5[N:27]=4)[CH3:25])=[N:20][CH:19]=[N:18][C:17]=3[N:16](COCC[Si](C)(C)C)[CH:15]=2)=[CH:5][N:4]=1.FC(F)(F)C(O)=O.N>>[CH3:1][O:2][C:3]1[C:8]([NH:9][S:10]([CH3:13])(=[O:11])=[O:12])=[CH:7][C:6]([C:14]2[C:22]3[C:21]([NH:23][C@H:24]([C:26]4[N:31]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:30](=[O:38])[C:29]5=[C:39]([CH3:42])[CH:40]=[CH:41][N:28]5[N:27]=4)[CH3:25])=[N:20][CH:19]=[N:18][C:17]=3[NH:16][CH:15]=2)=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131736140(S)-N-(2-Methoxy-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)pyridin-3-yl)methanesulfonamide

Product 1

HCID 73776509(S)-N-(2-Methoxy-5-(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)pyridin-3-yl)methanesulfonamideYield 32%

Procedure

(S)—N-(2-Methoxy-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)pyridin-3-yl)methanesulfonamide (82.5 mg, 0.12 mmol) was treated with trifluoroacetic acid (1.4 ml, 18.17 mmol) and a solution of ammonia (7N in methanol, 1.4 ml, 9.8 mmol) according to the method described in Example 27 to give 22 mg (32% yield) of the title compound as a white solid. Purity 95%.

Sources & evidence

ORD record
ord-ea58713951d34c499889aef20e66e77a
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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