Ethanol → HCID 70975371, compound

HRID 1023445Notes

Reaction equation

HRID 1023445 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([OH:18])([CH3:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:5]=[CH:4][N:3]=1.[C:19]([N:27]=C=O)(=[O:26])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[OH:18][C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:19]([NH2:27])=[O:26])[CH:7]=1)([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 69081523HCID 69081523, compound

Product 1

HCID 70975371HCID 70975371, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-(2-Amino-pyridin-4-yl)-1-o-tolyl-propan-2-ol (37 mg, 0.15 mmol) is dissolved in DCM (1 mL) and benzoyl isocynate (27 mg, 0.18 mmol) is added. The reaction is sealed and heated at 50° C. for 16 hrs. Then the solvent is removed and to the residue are added ethanol (1 mL) and potassium carbonate (32 mg, 0.23 mmol). The mixture is heated at 80° C. for 55 min. The solvent is removed and the residue is partitioned between water (25 mL) and EtOAc (35 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) followed by Gilson preparative HPLC affords 8.2 mg of the titled product.

Workup

  1. customThe reaction is sealed
  2. customThen the solvent is removed and to the residue
  3. temperatureThe mixture is heated at 80° C. for 55 min
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (25 mL) and EtOAc (35 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-80b5acb93e6e41df9efa37c5aa9814d7
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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