Potassium Carbonate → HCID 25234707, compound

HRID 1924455Notes

Reaction equation

HRID 1924455 reaction equation
[C:1]([C:5]1[C:6]([O:40][CH3:41])=[C:7]([CH:29]=[C:30]([N:32]2[CH:37]=[CH:36][C:35](=[O:38])[NH:34][C:33]2=[O:39])[CH:31]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=1[C:21]([N:23]1CCO[CH2:25][CH2:24]1)=[O:22])([CH3:4])([CH3:3])[CH3:2].N1C=CN=N1.C(=O)([O-])[O-].[K+].[K+]>C1S(=O)(=O)CCC1>[C:1]([C:5]1[C:6]([O:40][CH3:41])=[C:7]([CH:29]=[C:30]([N:32]2[CH:37]=[CH:36][C:35](=[O:38])[NH:34][C:33]2=[O:39])[CH:31]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[CH:12][C:11]=1[C:21]1[O:22][CH:25]=[CH:24][N:23]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25234704HCID 25234704, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 25234707HCID 25234707, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of the product from Example 27, Part A (80 mg, 0.15 mmol) in tetramethylene sulfone (1.5 ml) was added 1H-1,2,3-triazole (10 μL, 0.17 mmol) and potassium carbonate (73 mg, 0.53 mmol). The mixture was heated for 35 min at 130° C. in a microwave reactor. After cooling to room temperature, the mixture was partitioned between 1 N aqueous HCl (10 ml) and EtOAc (2×10 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 3% MeOH in CH2Cl2 as the eluent to give the title compound (37 mg, 46%). 1H NMR (300 MHz, DMSO-d6) 311.41 (d, J=1.84 Hz, 1 H) 10.10 (s, 1 H) 8.29 (d, J=1.10 Hz, 1 H) 8.05 (d, J=16.18 Hz, 1 H) 7.95 (d, J=8.82 Hz, 1 H) 7.82 (d, J=2.21 Hz, 1 H) 7.74 (d, J=8.09 Hz, 1 H) 7.51 (d, J=2.57 Hz, 1 H) 7.46 (d, J=0.74 Hz, 1 H) 7.39 (dd, J=8.64, 2.39 Hz, 1 H) 7.20-7.30 (m, 2 H) 5.65 (dd, J=7.91, 2.02 Hz, 1 H) 3.80 (s, 3 H) 3.07 (s, 3 H) 1.38 (s, 9 H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between 1 N aqueous HCl (10 ml) and EtOAc (2×10 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using 3% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-87feba07158c43de9dc0efc5a25584de
Source dataset
uspto-grants-2012_05
Patent number
US08178548B2

Reaction notes

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