Acetic Acid → N-{[4-({4-[(2-Aminopyridin-3-yl)methyl]piperazin-1-yl}carbonyl)-1,3-oxazol-2-yl]methyl}-N-cyclopropyl-4-methoxy-2,6-dimethylbenzenesulfonamide

HRID 469082Notes

Reaction equation

HRID 469082 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.[NH2:32][C:33]1[C:38]([CH:39]=O)=[CH:37][CH:36]=[CH:35][N:34]=1.CC(O)=O>ClCCCl>[NH2:32][C:33]1[C:38]([CH2:39][N:29]2[CH2:30][CH2:31][N:26]([C:24]([C:22]3[N:23]=[C:19]([CH2:18][N:4]([CH:1]4[CH2:2][CH2:3]4)[S:5]([C:8]4[C:9]([CH3:17])=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=4[CH3:14])(=[O:6])=[O:7])[O:20][CH:21]=3)=[O:25])[CH2:27][CH2:28]2)=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 58392961N-cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-(piperazin-1-ylcarbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide

Product 1

HCID 58393415N-{[4-({4-[(2-Aminopyridin-3-yl)methyl]piperazin-1-yl}carbonyl)-1,3-oxazol-2-yl]methyl}-N-cyclopropyl-4-methoxy-2,6-dimethylbenzenesulfonamide

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 2-amino-3-pyridinecarboxaldehyde (10 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-ce16d11a81c74b368064c4b52cd5d55c
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

Loading…