Trifluoroacetic acid → HCID 11720248, compound

HRID 1169835Notes

Reaction equation

HRID 1169835 reaction equation
[Cl:1][C:2]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:3]=1[C:4]([NH:6][C:7]([CH3:34])([C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:14][CH2:13][N:12]([S:15]([NH:18][CH2:19][CH2:20]C(OC(C)(C)C)=O)(=[O:17])=[O:16])[CH2:11][CH2:10]1)[CH3:8])=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:3]=1[C:4]([NH:6][C:7]([CH3:34])([C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:10][CH2:11][N:12]([S:15]([NH:18][CH2:19][CH3:20])(=[O:17])=[O:16])[CH2:13][CH2:14]1)[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68689530HCID 68689530, compound

Product 1

HCID 11720248HCID 11720248, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Dichloro-N-{1-methyl-1-[1-((tert-butoxycarbony)ethylaminosulfonyl)-4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (VI-2, 35 mg, 0.061 mmol) was dissolved in DCM (1.6 mL) and cooled in an ice bath. TFA (0.4 mL) was added dropwise and upon completion of the addition the reaction mixture was stirred in a nice bath for 0.5 h then allowed to warm to roomtemperature and stirred at room temperature for 12 h. The volatile components of the reaction mixture were removed in vacuo then saturated aqueous sodium hydrogen carbonate solution added dropwise. The mixture was extracted three times with EtOAc. The combined organic phase was dried (Na2SO4) and the solvent removed in vacuo to give 2,4-dichloro-N-{1-methyl-1-[1-(ethylaminosulfonyl)-4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (VI-3). 1H NMR (CD3OD, 500 MHz), δ 8.62 (d, J=4.1 Hz, 1H), 7.93 (m, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.48 (d, J=1.8 Hz, 1H), 7.37 (m, 1H), 7.30 (d, J=8.0 Hz, 1H), 3.66 (s, 2H), 3.48 (m, 2H), 3.00 (q, J=7.0 Hz, 2H), 2.94 (m, 2H), 2.50 (m, 2H), 2.04 (m, 2H), 1.12 (t, J=7.0 Hz, 3H); MS 472 (M+H).

Workup

  1. temperaturecooled in an ice bath
  2. temperatureto warm to roomtemperature
  3. stirringstirred at room temperature for 12 h
  4. customThe volatile components of the reaction mixture were removed in vacuo
  5. additionsaturated aqueous sodium hydrogen carbonate solution added dropwise
  6. extractionThe mixture was extracted three times with EtOAc
  7. dry with materialThe combined organic phase was dried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b48544b804f648ebb23dc9559d728e44
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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