Trifluoroacetic acid → HCID 178518093, compound

HRID 1367312Notes

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-44aac67215094f07a25fa92141f074b7
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893075B2

Reaction notes

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