1,4-Dioxane hydrochloride → (S)-(2-(4-(4-(1-(morpholin-2-ylmethyl)-1H-pyrazol-4-ylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)pyrimidin-5-yl)(phenyl)methanol

HRID 522655Notes

Reaction equation

HRID 522655 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:29]=[N:30][N:31]([CH2:33][C@H:34]5[O:39][CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]5)[CH:32]=4)[N:22]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>O1CCOCC1>[NH:36]1[CH2:37][CH2:38][O:39][CH:34]([CH2:33][N:31]2[CH:32]=[C:28]([NH:27][C:23]3[N:24]=[CH:25][N:26]=[C:21]([N:18]4[CH2:17][CH2:16][N:15]([C:12]5[N:11]=[CH:10][C:9]([C@H:1]([C:2]6[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=6)[OH:8])=[CH:14][N:13]=5)[CH2:20][CH2:19]4)[N:22]=3)[CH:29]=[N:30]2)[CH2:35]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118022966(S)-tert-butyl 2-((4-(4-(4-(5-benzoylpyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 118022373(S)-(2-(4-(4-(1-(morpholin-2-ylmethyl)-1H-pyrazol-4-ylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)pyrimidin-5-yl)(phenyl)methanolYield 35.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-((4-(4-(4-(5-benzoylpyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (80 mg, 0.127 mmol, crude) in dioxane (4 mL) was added 4 M HCl-dioxane (4 mL), and the reaction was stirred at room temperature overnight. LCMS showed the reaction was completed. The solvent was removed, and the residue was purified by Prep-HPLC to provide the title compound (S)-(2-(4-(4-(1-(morpholin-2-ylmethyl)-1H-pyrazol-4-ylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)pyrimidin-5-yl)(phenyl)methanol (Compound 189) (24.0 mg, 18%) as a yellowish solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-8ef91e68a65e4f7ea05318a707270611
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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