Ammonia → HCID 73776070, compound

HRID 1052733Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736182(S)-2-(1-((5-(4-Hydroxy-3-methoxyphenyl)-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 73776070HCID 73776070, compoundYield 46%

Procedure

(S)-2-(1-((5-(4-Hydroxy-3-methoxyphenyl)-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 (63 mg, 0.10 mmol) was treated with trifluoroacetic acid (1.26 ml, 16.36 mmol) and a solution of ammonia (7N in methanol, 1.26 ml, 8.82 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 6% n-hexane-ethyl acetate) to obtain 23 mg (46% yield) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (0% to 6% n-hexane-ethyl acetate)

Sources & evidence

ORD record: ord-3adf2a2f8e5e4dc6b6acc0e0ec22d9d1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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