Trifluoroacetic acid → HCID 178518093, compound

HRID 2261587Notes

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-af07f8f8df454312bc4d672d3018aa47
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846941B2

Reaction notes

Loading…