4-(2-Methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]benzoic acid → tert-butyl N-methyl-N-[3-(5-{4-(2-methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]phenyl}-1,2,4-oxadiazol-3-yl)benzyl]glycinate

HRID 219935Notes

Reaction equation

HRID 219935 reaction equation
[NH2:1][C:2](=[N:20][OH:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][N:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8].[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1[C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=O)=[CH:31][C:30]=1[NH:38][S:39]([CH3:42])(=[O:41])=[O:40]>>[CH3:8][N:7]([CH2:6][C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([C:2]2[N:1]=[C:33]([C:32]3[CH:36]=[CH:37][C:29]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]4[CH3:22])=[C:30]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:31]=3)[O:21][N:20]=2)[CH:4]=1)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 584433444-(2-Methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]benzoic acidHCID 72307500Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetate

Product 1

HCID 67528795tert-butyl N-methyl-N-[3-(5-{4-(2-methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]phenyl}-1,2,4-oxadiazol-3-yl)benzyl]glycinate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 51 (440.05 mg; 1.50 mmol), and Intermediate 25 (562.30 mg; 1.80 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography over Alumina column (c-hex/EtOAc: 9.5/0.5), affording the title compound as an off-white powder. HPLC (Method A) Rt 4.76 min (Purity: 96.7%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography over Alumina column (c-hex/EtOAc: 9.5/0.5)

Sources & evidence

ORD record
ord-da59ad06e12d4c528a6833d5c101c79e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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