Potassium Carbonate → HCID 73335820, compound

HRID 710654Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[C:4]2[CH2:11][O:10][CH2:9][CH2:8][C:5]=2[NH:6][N:7]=1.Cl[CH2:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C:20]2[N:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[N:25]=[CH:26][C:19]1=2)=[O:17].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C=O)C>[F:33][C:30]1[CH:31]=[CH:32][C:27]([N:24]2[C:20]3[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][N:6]4[C:5]5[CH2:8][CH2:9][O:10][CH2:11][C:4]=5[C:3]([C:2]([F:12])([F:1])[F:13])=[N:7]4)[C:19]=3[CH:26]=[N:25]2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 3-(trifluoromethyl)-1,4,6,7-tetrahydropyrano[4,3-c]pyrazole (0.050 g, 0.26 mmol), 2-chloro-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridine-4-yl]ethanone (0.050 g, 0.17 mmol) and K2CO3 (0.130 g, 0.94 mmol) in THF (0.8 mL) and DMF (0.4 mL) was heated at 55° C. for 1 hr. It was then cooled to rt. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.035 g, 55%). 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 7.44 (dd, J=8.8, 4.6 Hz, 2H), 7.17 (dd, J=8.8, 8.0 Hz, 2H), 5.13 (s, 2H), 4.75 (s, 2H), 3.98 (t, J=5.4 Hz, 2H), 3.87 (m, 2H), 2.85 (t, J=6.2 Hz, 2H), 2.79 (t, J=5.6 Hz, 2H), 2.10 (m, 2H); MS: (ES) m/z calculated for C21H19F4N5O2 [M+H]+ 450.1, found 450.1.

Workup

temperatureIt was then cooled to rt
customThe mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL)
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-c6e9c1a686554afe82d26e5a97f94f36
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181241B2

Reaction notes

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