Methanesulfonyl chloride → HCID 11496689, compound

HRID 1173419Notes

Reaction equation

HRID 1173419 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:11]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([N:11]([CH2:24][C:25]([F:26])([F:27])[F:28])[CH2:10][CH2:9][O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:3][CH:4]=2)=[CH:13][C:14]=1[C:20]([F:21])([F:22])[F:23])#[N:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86623733HCID 86623733, compound

Product 1

HCID 11496689HCID 11496689, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-[{2-[(4-aminophenyl)oxy]ethyl}(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.0423 g, 0.105 mmol) in dry pyridine (1 mL) at rt, under nitrogen, was added MsCl (0.010 mL, 0.12 mmol) in one portion. The mixture was stirred 22 h and concentrated in vacuo. The residue was partitioned between EtOAc and 10% v/v HCl and the layers were separated. The organic layer was washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.0372 g of the title compound as a colorless film: 1H NMR (300 MHz, CD3OD) δ 7.74 (d, J=8.8 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.26 (dd, J=8.8, 2.5 Hz, 1H), 7.19-7.12 (m, 2H), 6.90-6.83 (m, 2H), 4.43 (q, J=8.9 Hz, 2H), 4.22 (t, J=5.1 Hz, 2H), 4.04 (t, J=5.1 Hz, 2H), 2.85 (s, 3H); MS (APCI) m/z 480 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and 10% v/v HCl
  3. customthe layers were separated
  4. washThe organic layer was washed (water, brine)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-0053a7485cd1455eb74c40d0fe06d721
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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