Ammonia → (S)-N-(4-(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)-1H-indol-6-yl)methanesulfonamide

HRID 1052798Notes

Reaction equation

[O:1]=[C:2]1[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[N:5]=[C:4]([C@@H:11]([NH:13][C:14]2[C:15]3[C:22]([C:23]4[CH:31]=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:29]=[C:28]5[C:24]=4[CH:25]=[CH:26][NH:27]5)=[CH:21][N:20](COCC[Si](C)(C)C)[C:16]=3[N:17]=[CH:18][N:19]=2)[CH3:12])[N:3]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.FC(F)(F)C(O)=O.N>>[O:1]=[C:2]1[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[N:5]=[C:4]([C@@H:11]([NH:13][C:14]2[C:15]3[C:22]([C:23]4[CH:31]=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:29]=[C:28]5[C:24]=4[CH:25]=[CH:26][NH:27]5)=[CH:21][NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH3:12])[N:3]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736162(S)-N-(4-(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)-1H-indol-6-yl)methanesulfonamide

Product 1

HCID 118433719(S)-N-(4-(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)-1H-indol-6-yl)methanesulfonamideYield 18.9%

Procedure

(S)—N-(4-(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)-1H-indol-6-yl)methanesulfonamide (152 mg, 0.21 mmol) was treated with trifluoroacetic acid (1 ml, 12.9 mmol) and a solution of ammonia (7N in methanol, 5 mL, 35 mmol) according to the method described in Example 27 to give 23 mg (18% yield) of the title compound. Purity 98%.

Sources & evidence

ORD record: ord-1c71b234f72547b18286791877f5f2d0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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