Potassium Carbonate → HCID 57682722, compound

HRID 494229Notes

Reaction equation

[CH3:1][C:2]1([CH3:37])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:9][CH:10]=2)[CH:5](C(=O)C(F)(F)F)[NH:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:1][C:2]1([CH3:37])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:9][CH:10]=2)[CH2:5][NH:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of N-(4,4-dimethyl-1-trifluoroacetyl-1,2,3,4-tetrahydroisoquinol-7-yl)-4-(3-trifluoromethyl-2-pyridyl)-piperazine-1-carboxamide (30 mg, 0.057 mmol) and potassium carbonate (48 mg, 0.348 mmol) in methanol (4 ml) and water (4 ml) was heated at 50° C. for 6 h. After this period, the solvents were evaporated in vacuo and the residue partitioned between DCM (30 ml) and water (30 ml). The aqueous layer was re-extracted with DCM (2×30 ml) and then the combined organic layers dried (Na2SO4) and the solvents evaporated in vacuo to give the title compound as a white solid. 1H NMR (400 MHz, DMSO) δ (ppm): 8.45 (dd, 1H), 7.89 (dd, 1H), 7.22 (d, 1H), 7.10 (dd, 1H), 7.00-7.05 (m, 2H), 6.55 (s, 1H), 3.95 (s, 2H), 3.60-3.65 (m, 4H), 3.30-3.32 (m, 4H), 2.82 (s, 2H), 2.00 (br-s, 1H), 1.23 (s, 6H). MS (ES): MH+ 434.

Workup

waitAfter this period
customthe solvents were evaporated in vacuo
customthe residue partitioned between DCM (30 ml) and water (30 ml)
extractionThe aqueous layer was re-extracted with DCM (2×30 ml)
dry with materialthe combined organic layers dried (Na2SO4)
customthe solvents evaporated in vacuo

Sources & evidence

ORD record: ord-7369db5d608c434aa2afa77abef65939
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538121B2

Reaction notes

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