Ammonia → HCID 73508003, compound

HRID 1052775Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736213HCID 131736213, compound

Product 1

HCID 73508003HCID 73508003, compoundYield 44.9%

Procedure

(S)-2-(1-((5-(1H-Pyrrolo[2,3-b]pyridin-5-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 (51 mg, 0.08 mmol) was treated with trifluoroacetic acid (2 ml, 25 mmol) and a solution of ammonia (7N in methanol, 2 ml, 14 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 50% dichloromethane-2-propanol) to obtain 18 mg (44% yield) of the title compound. Purity 100%.

Workup

customThe residue was purified
customSP1® Purification System (0% to 50% dichloromethane-2-propanol)

Sources & evidence

ORD record: ord-36f330dfa77b491aaea9bc600419f2d9
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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