Trifluoroacetic acid → HCID 178518093, compound

HRID 1952060Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12](Cl)[C:11]([CH:15]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=[O:38]>C(#N)C>[NH:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([CH2:15][C:11]2[C:12]([OH:38])=[N:13][C:8]([NH:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)=[CH:18]1

Participants

Conditions

Temperature: 85 °C

Procedure

To (6-(4-chlorobenzylamino)-2-chloropyridin-3-yl)(1H-pyrrolo[2,3-b]pyridin-3-yl)methanol (P-0050, 0.028 g, 0.000070 mol) dissolved in acetonitrile (1 mL) was added triethylsilane (42.6 uL, 0.000266 mol) and trifluoroacetic acid (28.4 uL, 0.000368 mol). The reaction was heated at 85° C. overnight. The reaction was extracted with ethyl acetate and saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane, 3%, 5% and finally 10% methanol in dichloromethane to give the compound as a white solid (P-0051, 20 mg, 78%). MS (ESI) [M+H+]+=365.3.

Workup

extractionThe reaction was extracted with ethyl acetate and saturated sodium bicarbonate
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by silica gel column chromatography
washeluting with dichloromethane, 3%, 5% and finally 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-d3af809e20e84484b846af3a0da28b9b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404700B2

Reaction notes

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