Ammonia → (S)-2-(1-((5-(1-(3-(Dimethylamino)propyl)-1H-pyrazol-4-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 1052750Notes

Reaction equation

[CH3:1][N:2]([CH3:48])[CH2:3][CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([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)[CH:8]=[N:7]1.FC(F)(F)C(O)=O.N>>[CH3:48][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([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)[CH:8]=[N:7]1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736248(S)-2-(1-((5-(1-(3-(Dimethylamino)propyl)-1H-pyrazol-4-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 90102695(S)-2-(1-((5-(1-(3-(Dimethylamino)propyl)-1H-pyrazol-4-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 44.7%

Procedure

(S)-2-(1-((5-(1-(3-(Dimethylamino)propyl)-1H-pyrazol-4-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 (50 mg, 0.05 mmol) was treated with trifluroacetic acid (2 ml, 26 mmol) and a solution of ammonia (7N in methanol, 5 ml, 35 mmol) according to the method decried in Example 27 to give 12 mg (42% yield) of the title compound. Purity 97%.

Sources & evidence

ORD record: ord-7f83588b868a4bbcafbab5431afde870
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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