Dichloromethane → HCID 58788270, compound

HRID 2374742Notes

Reaction equation

HRID 2374742 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]([O:15][C:16](=[O:40])[CH2:17][NH:18][C:19]1[C:23]([C:24](=[O:38])[NH:25][C:26](=O)[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=2[F:36])=[CH:22][N:21]([CH3:39])[N:20]=1)[CH3:14].ClCCl>C1(C)C=CC=CC=1>[CH2:13]([O:15][C:16](=[O:40])[CH2:17][N:18]1[C:19]2=[N:20][N:21]([CH3:39])[CH:22]=[C:23]2[C:24](=[O:38])[N:25]=[C:26]1[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1[F:36])[CH3:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 58788310HCID 58788310, compound

Product 1

HCID 58788270HCID 58788270, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of p-toluenesulfonic acid monohydrate (200 mg) and 2-(4-(3-(2,3-difluorophenyl)-propanoylcarbamoyl)-1-methyl-1H-pyrazol-3-ylamino)-acetic acid ethyl ester (Int B60) (1.2 g, 3.04 mmol) in toluene (100 ml) was refluxed for 3 h. The mixture was cooled and dichloromethane (200 ml) was added. The resulting solution was washed with aqueous sodium bicarbonate solution, brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (silica, 5% methanol/dichloromethane) to give the title compound as a cream solid (650 mg, 57%). 1H-NMR (DMSO) δ 1.20 (3H, t), 2.94-3.09 (4H, m), 3.95 (3H, s), 4.18 (2H, q), 5.05 (2H, s), 7.11-7.29 (3H, m), 8.39 (1H, s); MS (APCI+) found (M+1)=377; C18H18F2N4O3 requires 376.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperatureThe mixture was cooled
  3. washThe resulting solution was washed with aqueous sodium bicarbonate solution, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a07c6a31e9f742e9a260b5a6e5fd2feb
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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