Ammonia → (S)-N-Methyl-N-(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)phenyl)methanesulfonamide

HRID 1052814Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736167(S)-N-Methyl-N-(3-(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)methanesulfonamide

Product 1

HCID 90101983(S)-N-Methyl-N-(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)phenyl)methanesulfonamideYield 90.6%

Procedure

(S)—N-Methyl-N-(3-(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)methanesulfonamide (143 mg, 0.20 mmol) was treated with trifluoroacetic acid (3.8 ml, 49 mmol) and a solution of ammonia (7N in methanol, 3.8 ml, 27 mmol) according to the method described in Example 27 to give 103 mg (86% yield) of the title compound. Purity 96%.

Sources & evidence

ORD record: ord-dc3aec63e7f2416692e99b6056b7cc41
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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