Dichloromethane → HCID 86670798, compound

HRID 878238Notes

Reaction equation

HRID 878238 reaction equation
C(OC[N:10]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N:21]([CH3:38])[C:22](=[O:37])[C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)=[C:13]([CH3:39])[CH:12]=[N:11]1)C1C=CC=CC=1.C(Cl)Cl>C(O)(C(F)(F)F)=O>[CH3:38][N:21]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[C:14]1[NH:10][N:11]=[CH:12][C:13]=1[CH3:39])[C:22](=[O:37])[C:23]1[CH:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=[C:25]([C:33]([F:34])([F:35])[F:36])[CH:24]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86670799HCID 86670799, compound

Product 1

HCID 86670798HCID 86670798, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-[4-(2-benzyloxymethyl-4-methyl-2H-pyrazol-3-yl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide (70 mg, 128 μmol) in TFA (3 mL) was added CH2Cl2 (300 μL). The reaction mixture was stirred at 80° C. for 2 hours and then concentrated in vacuum. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless foam (20 mg, 37%). MS (ESI): m/z=429.114 [M+H]+.

Workup

  1. concentrationconcentrated in vacuum
  2. additionThe reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  5. washThe organic layers were washed with 30 mL brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe compound was purified by silica gel chromatography on a 20 g column
  10. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-5655da3ea350416a8fe2e96a6c8a79eb
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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