Trifluoroacetic acid → HCID 86645579, compound

HRID 2383439Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].COC1C=CC(C[N:15]2[C:19]3[N:20]=[CH:21][C:22]4[CH2:23][N:24]([C:28](=[O:37])[C@H:29]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[NH3+:30])[CH2:25][CH2:26][C:27]=4[C:18]=3[CH:17]=[N:16]2)=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH:17]1[C:18]2[C:27]3[CH2:26][CH2:25][N:24]([C:28](=[O:37])[C@H:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[NH3+:30])[CH2:23][C:22]=3[CH:21]=[N:20][C:19]=2[NH:15][N:16]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To (S)-2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethanaminium 2,2,2-trifluoroacetate (0.109 g, 0.18 mmol) was added trifluoroacetic acid (2 mL). The reaction mixture was heated at 65° C. for 16 hours. On completion of the reaction, toluene (5 mL) was added followed by removal of the solvent under reduced pressure. The mixture was evaporated to dryness in the Genevac and a dark brown solid was obtained. The crude product was purified using reverse phase HPLC to give the pure desired product, (S)-2-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethanaminium 2,2,2-trifluoroacetate as a pale yellow solid (0.082 g, 84%). M.p.>100° C.; 1H NMR (400 MHz, DMSO-d6) δ12.75 (brs, 1H), 8.62 (brs, 2H), 8.39/8.13 (s, 1H, rotamers), 8.08/8.06 (s, 1H, rotamers), 7.56-7.35 (m, 5H), 5.74 (m, 1H), 4.91 (m, 2H), 3.73 (m, 2H), 3.08 (m, 2H); LCMS [M+H]: 308.

Workup

additionwas added
customfollowed by removal of the solvent under reduced pressure
customThe mixture was evaporated to dryness in the Genevac
customa dark brown solid was obtained
customThe crude product was purified

Sources & evidence

ORD record: ord-0e2ece2f0b5548669b50c59e8c698be5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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