Potassium Carbonate → HCID 68857447, compound

HRID 1453897Notes

Reaction equation

HRID 1453897 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(OC(=O)[NH:16][CH:17]([CH3:31])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([OH:30])[C:26]=2[CH:28]=O)[CH:21]=[N:20]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[CH3:6][O:5][C:3]([C:2]1[O:30][C:25]2=[CH:24][CH:23]=[C:22]3[C:27]([N:19]([CH2:18][C@@H:17]([NH2:16])[CH3:31])[N:20]=[CH:21]3)=[C:26]2[CH:28]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 136395573HCID 136395573, compound

Product 1

HCID 68857447HCID 68857447, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a 50 mL round bottom flask containing NMP (20 mL), methyl bromoacetate (0.35 g 2.3 mmol), and [2-(7-formyl-6-hydroxy-indazol-1-yl)-1-methyl-ethyl]-carbamic acid benzyl ester (0.751 g, 2.1 mmol) was added K2CO3 (1.4 g, 10 mmol). This mixture was heated to 90° C. for 16 h, then allowed to cool to 23° C., decanted into a saturated aqueous NaHCO3 solution (50 mL), and extracted with ethyl acetate (2×20 mL). The combined extracts were dried (Na2SO4), filtered and concentrated. The crude product was purified by chromatography (silica gel, hexanes: ethyl acetate gradient, 3:1 to 1:1) to provide an oil: LC/MS m/z 408 [M+H]+; 1H NMR (D2O): δ 8.19 (s, 1H), 8.06 (s, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.30 (bm, 4H), 5.15 (d, 1H), 5.08 (dd, 2H), 4.8 (m, 1H), 4.6 (m, 1H), 4.29 (m, 1H), 4.01 (s, 3H), 1.19 (d, J=6.6 Hz, 3H).

Workup

  1. temperatureto cool to 23° C.
  2. customdecanted into a saturated aqueous NaHCO3 solution (50 mL)
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (silica gel, hexanes: ethyl acetate gradient, 3:1 to 1:1)
  8. customto provide an oil

Sources & evidence

ORD record
ord-351648a8cc0342ef971cad5514d78c34
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

Loading…