Acetic Acid → N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-({4-[(3-methyl-1H-pyrazol-4-yl)methyl]piperazin-1-yl}carbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide

HRID 469084Notes

Reaction equation

HRID 469084 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH3:32][C:33]1[C:37]([CH:38]=O)=[CH:36][NH:35][N:34]=1.CC(O)=O>ClCCCl>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH2:38][C:37]4[C:33]([CH3:32])=[N:34][NH:35][CH:36]=4)[CH2:28][CH2:27]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:9]([CH3:17])=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=2[CH3:14])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 58392961N-cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-(piperazin-1-ylcarbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamideHCID 1784345503-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 178491754N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-({4-[(3-methyl-1H-pyrazol-4-yl)methyl]piperazin-1-yl}carbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of N-cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-(piperazin-1-ylcarbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide (30 mg, 0.07 mmol) in DCE (2 mL) were added 3-methyl-1H-pyrazole-4-carboxaldehyde (9 mg, 0.08 mmol) and AcOH (3 μL, 0.07 mmol) and the reaction mixture was stirred for 1 h at ambient temperature. STAB (20 mg, 0.09 mmol) was added and the reaction was stirred for 16 h. The reaction mixture was quenched with H2O (2 mL) and extracted with DCM (3×2 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep method D to afford the title compound.

Workup

  1. additionSTAB (20 mg, 0.09 mmol) was added
  2. stirringthe reaction was stirred for 16 h
  3. customThe reaction mixture was quenched with H2O (2 mL)
  4. extractionextracted with DCM (3×2 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-56c7d2d8923245d28d24716789994b48
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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