Potassium Carbonate → HCID 57682734, compound

HRID 494224Notes

Reaction equation

HRID 494224 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)[N:5](C(=O)C(F)(F)F)[CH2:4][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)[NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86605994HCID 86605994, compound

Product 1

HCID 57682734HCID 57682734, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(4,4-dimethyl-1-trifluoroacetyl-1,2,3,4-tetrahydroquinol -7-yl)-4-(3-trifluoromethyl-2-pyridyl)-piperazine-1-carboxamide (50 mg, 0.0955 mmol) and potassium carbonate (40 mg, 0.287 mmol) in methanol (5 ml) and water (5 ml) was heated at 60° C. for 4 h. After this period, the solvents were evaporated in vacuo and the residue partitioned between DCM (50 ml) and water (30 ml). The aqueous layer was re-extracted with DCM (3×50 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, CDCl3) δ (ppm): 8.45 (dd, 1H), 7.90 (dd, 1H), 7.00-7.05 (m, 2H), 6.70 (d, 1H), 6.70 (d, 1H), 6.43 (dd, 1H), 6.32 (br-s, 1H), 3.60-3.65 (br, 4H), 3.20-3.30 (m, 6H), 1.65-1.70 (m, 2H), 1.26 (s, 6H). MS (ES): MH+ 434.

Workup

  1. waitAfter this period
  2. customthe solvents were evaporated in vacuo
  3. customthe residue partitioned between DCM (50 ml) and water (30 ml)
  4. extractionThe aqueous layer was re-extracted with DCM (3×50 ml)
  5. dry with materialthe combined organic layers dried (Na2SO4)
  6. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-fee122d3eeab44ea971875870de47760
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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