Tetrahydrofuran → HCID 10150432, compound

HRID 2105575Notes

Reaction equation

HRID 2105575 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:24])/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[N:2]1.C1COCC1.[N:30]([CH3:33])=[C:31]=[O:32]>CCOC(C)=O>[C:20]([C:17]1[CH:16]=[CH:15][C:14](/[CH:13]=[CH:12]/[C:11]([NH:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[N:2][N:1]3[C:31](=[O:32])[NH:30][CH3:33])=[CH:5][CH:6]=2)=[O:24])=[CH:19][CH:18]=1)([CH3:21])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12228Methyl IsocyanateHCID 57808190HCID 57808190, compound

Product 1

HCID 10150432HCID 10150432, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottomed flask, equipped with a magnetic stir bar, was added (2E)-N-(1H-indazol-6-yl)-3-[4-(tert-butyl)phenyl]prop-2-enamide, Example 155, (61 mg, 0.19 mmol), THF (8 mL) and isocyanatomethane (54 mg, 0.96 mmol, Carbolabs). The reaction mixture was stirred at room temperature for 8 h. The reaction mixture was diluted with EtOAc (10 mL), washed with water (8 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (40:20:1 hexane:EtOAc:MeOH) provided the title product as an off-white solid. MP 208-209° C. MS (ESI, pos. ion) m/z: 377 (M+1).

Workup

  1. customTo a round-bottomed flask, equipped with a magnetic stir bar
  2. washwashed with water (8 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (40:20:1 hexane:EtOAc:MeOH)

Sources & evidence

ORD record
ord-e6760317a7e741d4891ad456c71a3dbd
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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