Ammonia → (S)-2-(1-((5-(1-(2-Methoxybenzyl)-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052787Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:51]=[CH:50][CH:49]=[CH:48][C:4]=1[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([NH:20][C@H:21]([C:23]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:27](=[O:35])[C:26]5=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]5[N:24]=4)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=3[N:13](COCC[Si](C)(C)C)[CH:12]=2)=[N:7]1.FC(F)(F)C(O)=O.N>>[CH3:1][O:2][C:3]1[CH:51]=[CH:50][CH:49]=[CH:48][C:4]=1[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([NH:20][C@H:21]([C:23]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:27](=[O:35])[C:26]5=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]5[N:24]=4)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)=[N:7]1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736239(S)-2-(1-((5-(1-(2-Methoxybenzyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 136623666(S)-2-(1-((5-(1-(2-Methoxybenzyl)-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 105%

Procedure

(S)-2-(1-((5-(1-(2-Methoxybenzyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (16 mg, 0.02 mmol) was treated with trifluoroacetic acid (500 μl, 6.49 mmol) and a solution of ammonia (7N in methanol, 500 μl, 3.50 mmol) according to the method described in Example 27 to obtain 12 mg (87% yield) of the title compound without further purification.

Sources & evidence

ORD record: ord-8923200f4ec444ceb427f9b31e1b5054
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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