Diethyl Ether → HCID 57677459, compound

HRID 492834Notes

Reaction equation

HRID 492834 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([NH:16][CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[O:15])[CH:8]=2)=[C:4]([F:26])[CH:3]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[C:42]1([CH2:48][C:49]([N:51]=[C:52]=[S:53])=[O:50])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(OCC)C>C(O)C.C1(C)C=CC=CC=1.CCCCCC>[F:26][C:4]1[CH:3]=[C:2]([NH:1][C:52]([NH:51][C:49](=[O:50])[CH2:48][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[S:53])[CH:25]=[CH:24][C:5]=1[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[O:15])[CH:8]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 12454157Phenylacetyl isothiocyanateHCID 23153004HCID 23153004, compound

Product 1

HCID 57677459HCID 57677459, compoundYield 18.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

1-[6-(4-Amino-2-fluorophenoxy)pyrimidin-4-yl]-3-(1-methylpiperidin-4-yl)urea (50 mg) was dissolved in ethanol, and then D-10-camphorsulfonic acid (64.6 mg) was added thereto, followed by stirring for 5 min. A solution of phenylacetyl isothiocyanate in toluene (1.5 ml) was added thereto, followed by stirring for 4 hrs. The reaction mixture was partitioned between ethyl acetate (30 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether (0.5 ml)-hexane (2.0 ml) was then added to suspend. The solid was filtered off, and dried under aeration to provide the titled compound (13.5 mg, 18.1%) as white powder.

Workup

  1. stirringby stirring for 4 hrs
  2. customThe reaction mixture was partitioned between ethyl acetate (30 ml)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate)
  8. additionFractions containing the target compound
  9. concentrationwere concentrated
  10. customto give a residue
  11. filtrationThe solid was filtered off
  12. customdried under aeration

Sources & evidence

ORD record
ord-9ca1bfcc549b4d3782ac0e0af83d2f4c
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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