Dimethylformamide → HCID 68932611, compound

HRID 32122Notes

Reaction equation

HRID 32122 reaction equation
[C:1]1([CH:7]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:37][NH:38][CH:39]1[C:48]2[C:43](=[CH:44][C:45]([CH2:49][N:50]3[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]3)=[CH:46][CH:47]=2)[O:42][CH2:41][CH2:40]1>C(Cl)Cl>[CH3:37][N:38]([CH:39]1[C:48]2[C:43](=[CH:44][C:45]([CH2:49][N:50]3[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]3)=[CH:46][CH:47]=2)[O:42][CH2:41][CH2:40]1)[C:9](=[O:11])[CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[CH:17]=1)(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 454390913-Phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acidHCID 68705889HCID 68705889, compound

Product 1

HCID 68932611HCID 68932611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acid (100 mg, 0.268 mmol, 1.0 eq) and DMF (one small drop) in CH2Cl2 (2.5 mL) was added oxalyl chloride (68 mg, 0.536 mmol, 2.0 eq). The reaction was stirred at 0° C. for 1 h. It was warmed to RT and stirred at RT for additional 15 min. Solvent was removed with a rotary evaporator. The newly formed acid chloride was dissolved in CH2Cl2 (2 mL) and the solution was cooled down to 0° C. A solution of methyl-(7-piperidin-1-ylmethyl-chroman-4-yl)-amine (70 mg, 0.268 mmol, 1.0 eq) in CH2Cl2 (0.95 mL) was added slowly. The resulting mixture was stirred at 0° C. for 20 min. The mixture was warmed to RT and stirred at this temperature for additional 20 min. The reaction was quenched with saturated Na2CO3 (60 mL) The crude was extracted with CH2Cl2 (60 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Flash column chromatography (silica gel, 0-4% MeOH—CH2Cl2) afforded the title compound as a colorless thin film. MS (ESI, pos. ion) m/z: 616 (M+1).

Workup

  1. temperatureIt was warmed to RT
  2. stirringstirred at RT for additional 15 min
  3. customSolvent was removed with a rotary evaporator
  4. dissolutionThe newly formed acid chloride was dissolved in CH2Cl2 (2 mL)
  5. temperaturethe solution was cooled down to 0° C
  6. stirringThe resulting mixture was stirred at 0° C. for 20 min
  7. temperatureThe mixture was warmed to RT
  8. stirringstirred at this temperature for additional 20 min
  9. customThe reaction was quenched with saturated Na2CO3 (60 mL) The crude
  10. extractionwas extracted with CH2Cl2 (60 mL×3)
  11. washThe extract phase was washed with saturated NaCl
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-a2ea8bab25504c45bbeda3778273e4bf
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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