Ammonia → HCID 90102751, compound

HRID 1052847Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736228HCID 131736228, compound

Product 1

HCID 90102751HCID 90102751, compoundYield 43%

Procedure

(S)-1-(2-Methoxy-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)pyridin-3-yl)urea (60 mg, 0.08 mmol, 86% purity) was treated with trifluoroacetic acid (2.0 ml, 26.0 mmol) and a solution of ammonia (7N in methanol, 5.0 ml, 35.0 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (reverse phase, 0% to 100% water-methanol/acetonitrile 1:1) to obtain 18 mg (43% yield) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (reverse phase, 0% to 100% water-methanol/acetonitrile 1:1)

Sources & evidence

ORD record: ord-788f5605df0c4e09b8a70bfef1791491
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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