Ammonia → HCID 90102223, compound

HRID 1052833Notes

Reaction equation

[NH2:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[C:22]4[C:21]([NH:23][C@H:24]([C:26]5[N:31]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)[C:30](=[O:38])[C:29]6=[C:39]([CH3:42])[CH:40]=[CH:41][N:28]6[N:27]=5)[CH3:25])=[N:20][CH:19]=[N:18][C:17]=4[N:16](COCC[Si](C)(C)C)[CH:15]=3)[CH:10]=[C:11]([OH:13])[CH:12]=2)=[N:4][N:3]=1.FC(F)(F)C(O)=O.N>>[NH2:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[C:22]4[C:21]([NH:23][C@H:24]([C:26]5[N:31]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)[C:30](=[O:38])[C:29]6=[C:39]([CH3:42])[CH:40]=[CH:41][N:28]6[N:27]=5)[CH3:25])=[N:20][CH:19]=[N:18][C:17]=4[NH:16][CH:15]=3)[CH:10]=[C:11]([OH:13])[CH:12]=2)=[N:4][N:3]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736244HCID 131736244, compound

Product 1

HCID 90102223HCID 90102223, compoundYield 15%

Procedure

(S)-2-(1-((5-(3-(5-Amino-1,3,4-oxadiazol-2-yl)-5-hydroxyphenyl)-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 (40 mg, 0.06 mmol) was treated with trifluoroacetic acid (1 ml, 13 mmol) and a solution of ammonia (7N in methanol, 1 ml, 59 mmol) according to the method described in Example 27. The residue was purified by reverse phase chromatography using SP1® Purification System to give 5 mg (15% yield) of the title compound. Purity 98%.

Workup

customThe residue was purified by reverse phase chromatography
customSP1® Purification System

Sources & evidence

ORD record: ord-92bfa4f72a8b4f83a7fb45e5a1993977
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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