p-Toluenesulfonic acid → HCID 46206559, compound

HRID 1410466Notes

Reaction equation

HRID 1410466 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:28]2[CH:36]=[C:35]3[C:31]([CH:32]=[CH:33][NH:34]3)=[CH:30][CH:29]=2)[O:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)(=[O:3])[NH2:2].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[NH:34]1[C:35]2[C:31](=[CH:30][CH:29]=[C:28]([C:6]3[O:7][C:8]([C:9]4[CH:10]=[CH:11][C:12]([N:15]5[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]5)=[CH:13][CH:14]=4)=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=3)[CH:36]=2)[CH:32]=[CH:33]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68634136HCID 68634136, compound

Product 1

HCID 46206559HCID 46206559, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(4-(4-carbamoyl-2-(1H-indol-6-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.018 g, 0.04 mmol) in MeOH was loaded onto a MP-TsOH cartridge (500 mg). The cartridge was washed with MeOH and allowed to stand for 2 hours. The cartridge was then washed with 2M ammonia in MeOH and the solvent removed in vacuo. The residue was purified by preparative HPLC to afford 2-(1H-indol-6-yl)-5-(4-(piperazin-1-yl)phenyl)oxazole-4-carboxamide (0.006 g, 0.02 mmol, 50%). 1H NMR (DMSO) δ 2.85 (4H, t), 3.20 (4H, t), 6.55 (1H, m), 7.04 (2H, d), 7.55 (1H, br. s), 7.56 (1H, m), 7.68 (1H, br. s), 7.71 (1H, d), 7.77 (1H, dd), 8.15 (1H, s), 8.26 (2H, d), 11.48 (1H, br. s). LCMS (2) Rt: 2.32 min; m/z (ES+) 388.

Workup

  1. washThe cartridge was washed with MeOH
  2. washThe cartridge was then washed with 2M ammonia in MeOH
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d83f2304edd0413c9d3edcd6cb90cc23
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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