p-Toluenesulfonic acid → HCID 118023252, compound

HRID 522647Notes

Reaction equation

HRID 522647 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]4[CH:28]=[N:29][N:30]([CH2:32][CH:33]5[CH2:37][O:36]C(C)(C)[O:34]5)[CH:31]=4)[N:21]=3)[CH2:16][CH2:15]2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>ClC(Cl)C.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]4[CH:28]=[N:29][N:30]([CH2:32][CH:33]([OH:34])[CH2:37][OH:36])[CH:31]=4)[N:21]=3)[CH2:16][CH2:15]2)=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 118023134HCID 118023134, compound

Product 1

HCID 118023252HCID 118023252, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)-N-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1,3,5-triazin-2-amine (200 mg, 0.3 mmol), and p-TSA (40 mg, 0.2 mmol) in dichloroethane (2.5 mL) was stirred at 80° C. under N2 overnight. LCMS showed the reaction was completed. The reaction mixture was cooled to RT and diluted with ethyl acetate (40 mL). The organic phase was washed with water (30 mL) and brine (30 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by Prep-HPLC to give 3-(4-(4-(4-(5-benzylpyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)propane-1,2-diol (13.8 mg, yield 7%) as a white solid. MS (ES+) C24H28N10O2 requires: 488, found: 489 [M+H]+.

Workup

  1. washThe organic phase was washed with water (30 mL) and brine (30 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-89a7ba1b82e643b28bf84efed2bae57d
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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