p-Toluenesulfonic acid → HCID 44467389, compound

HRID 2281394Notes

Reaction equation

HRID 2281394 reaction equation
N1(O[C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH:20]([CH2:23][NH:24]C(=O)OC(C)(C)C)[CH2:19][CH2:18]3)[C:14]([C:32](=[O:34])[NH2:33])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][N:45]([C:48](=[O:50])[CH3:49])[CH2:44][CH2:43]2)=[CH:38][CH:37]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[C:48]([N:45]1[CH2:44][CH2:43][N:42]([C:39]2[CH:40]=[CH:41][C:36]([NH:35][C:11]3[N:16]=[C:15]([N:17]4[CH2:18][CH2:19][CH:20]([CH2:23][NH2:24])[CH2:21][CH2:22]4)[C:14]([C:32]([NH2:33])=[O:34])=[CH:13][N:12]=3)=[CH:37][CH:38]=2)[CH2:47][CH2:46]1)(=[O:50])[CH3:49]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 57990388HCID 57990388, compound

Product 1

HCID 44467389HCID 44467389, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of tert-butyl (1-(2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-5-carbamoylpyrimidin-4-yl)piperidin-4-yl)methylcarbamate (138 mg, 0.294 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (84 mg, 0.38 mmol) and p-toluenesulfonic acid (56 mg, 0.294 mmol) in dioxane (4 mL) was stirred at 100° C. for 3 h. dioxane was removed in vacuo. The residue was dissolved in CH2C12 (5 mL) and TFA (5 mL). The solution was stirred at room temperature for 30 min. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (15 mg). MS 453.6 (M+H); UV 222.8, 263.8 nm.

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in CH2C12 (5 mL) and TFA (5 mL)
  3. concentrationIt was then concentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-1c90cb74b8194a8ca2a3e5e0136ae745
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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