Dimethylformamide dimethyl acetal → HCID 44591764, compound

HRID 1441238Notes

Reaction equation

HRID 1441238 reaction equation
[Cl:1][C:2]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([C:22]2[C:27]([F:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:13][CH2:12][N:11]([S:14]([C:17]2[N:18]=[N:19][NH:20][CH:21]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:5].[CH3:34]OC(OC)N(C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([C:22]2[C:27]([F:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:9][CH2:10][N:11]([S:14]([C:17]2[N:18]=[N:19][N:20]([CH3:34])[CH:21]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)=[O:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178522751HCID 178522751, compound

Product 1

HCID 44591764HCID 44591764, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2,4-dichloro-N-{[4-(3-fluoropyridin-2-yl)-1-[(1H-1,2,3-triazol-4-yl)sulfonyl]piperidin-4-yl]methyl}benzamide (0.15 g; 0.29 mmol) in toluene (5 ml) was added N,N-dimethylformamide dimethyl acetal (0.35 g; 0.4 ml; 2.92 mmol) and the mixture heated at reflux for 1 hour. The solvent was removed under vacuum and the residue azeotroped twice with toluene. The crude product was purified by preparative TLC on silica gel eluted with 3% methanol in DCM to give the title compound as the most polar isomer.(30 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed under vacuum
  4. customthe residue azeotroped twice with toluene
  5. customThe crude product was purified by preparative TLC on silica gel
  6. washeluted with 3% methanol in DCM

Sources & evidence

ORD record
ord-89b8079309284d00944395508b817631
Source dataset
uspto-grants-2010_02
Patent number
US07655644B2

Reaction notes

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