Trifluoroacetic acid → 7-(phenylsulfonyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

HRID 2383451Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([S:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)(=[O:23])=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:24]1([S:21]([N:17]2[CH2:16][C:15]3[CH:14]=[N:13][C:12]4[NH:8][N:9]=[CH:10][C:11]=4[C:20]=3[CH2:19][CH2:18]2)(=[O:23])=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To 3-(4-methoxybenzyl)-7-(phenylsulfonyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.109 g, 2.51 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. The reaction mixture was evaporated to dryness under reduced pressure to yield a dark brown solid. The crude product was purified using reverse phase HPLC chromatography to give the desired product, 7-(phenylsulfonyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a white solid (0.043 g, 54%). M.p.=270-271° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.59 (s, 1H), 8.33 (s, 1H), 8.1 (d, J=1.2 Hz, 1H), 7.88-7.84 (m, 2H), 7.73-7.61 (m, 3H), 4.35 (s, 2H), 3.43 (t, J=5.6 Hz, 2H), 3.14 (t, J=6.4 Hz, 2H); LCMS [M+H]: 315.

Workup

additionwas added
customThe reaction mixture was evaporated to dryness under reduced pressure
customto yield a dark brown solid
customThe crude product was purified

Sources & evidence

ORD record: ord-a2b63b6154a642519e9ea30b8f2e32e6
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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