Potassium Carbonate → HCID 10173307, compound

HRID 1296727Notes

Reaction equation

HRID 1296727 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][N:12]=[C:11]2[S:16][CH3:17])=O.Cl.[CH:27]1([NH:32][C:33]([NH2:35])=[NH:34])[CH2:31][CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH:27]1([NH:32][C:33]2[N:35]=[C:5]([C:7]3[C:8]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)=[N:9][N:10]4[C:15]=3[CH:14]=[CH:13][N:12]=[C:11]4[S:16][CH3:17])[CH:4]=[CH:3][N:34]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69449408HCID 69449408, compoundHCID 178479367HCID 178479367, compound

Product 1

HCID 10173307HCID 10173307, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (2E)-3-(dimethylamino)-1-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]prop-2-en-1-one (660 mg, 1.85 mmol) and N-cyclopentylguanidine hydrochloride (600 mg, 3.71 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (760 mg, 5.55 mmol). The reaction mixture was heated to 100° C. for 1 hour and then to 115° C. for 4 hours. The reaction was allowed to cool to room temperature and diluted with water. The mixture was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel chromatography eluting with 50% acetone in dichloromethane to yield N-cyclopentyl-4-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine (210 mg, 32%). 1H NMR (CDCl3): δ 8.05(d,1H), 7.94 (m, 2H), 7.64 (dd, 2H), 7.13 (t, 2H), 6.29 (d, 1H), 5.21 (bs, 1H), 4.31 (m, 1H), 2.72 (s, 3H), 2.06 (m, 2H), 1.49–1.82 (m, 6H). MS m/z 421 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. washeluting with 50% acetone in dichloromethane

Sources & evidence

ORD record
ord-d35b582d94884a9bb322f8eed1017e19
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

Loading…