Trifluoroacetic acid → N-(1-((S)-morpholin-2-ylmethyl)-1H-pyrazol-4-yl)-4-(4-(5-(1-phenylethyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-amine

HRID 522635Notes

Reaction equation

HRID 522635 reaction equation
[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[N:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]5[CH:29]=[N:30][N:31]([CH2:33][C@H:34]6[O:39][CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]6)[CH:32]=5)[N:22]=4)[CH2:17][CH2:16]3)=[N:13][CH:14]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[NH:36]1[CH2:37][CH2:38][O:39][C@H:34]([CH2:33][N:31]2[CH:32]=[C:28]([NH:27][C:23]3[N:22]=[C:21]([N:18]4[CH2:17][CH2:16][N:15]([C:12]5[N:11]=[CH:10][C:9]([CH:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)[CH3:8])=[CH:14][N:13]=5)[CH2:20][CH2:19]4)[N:26]=[CH:25][N:24]=3)[CH:29]=[N:30]2)[CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118023199(2S)-tert-butyl 2-((4-(4-(4-(5-(1-phenylethyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 118023388N-(1-((S)-morpholin-2-ylmethyl)-1H-pyrazol-4-yl)-4-(4-(5-(1-phenylethyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-tert-butyl 2-((4-(4-(4-(5-(1-phenylethyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (130 mg, crude) in dichloromethane (6 mL) was dropwise added trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for 0.5 hour and then concentrated. The residue was purified by Prep-HPLC to provide N-(1-((S)-morpholin-2-ylmethyl)-1H-pyrazol-4-yl)-4-(4-(5-(1-phenylethyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-amine as a white solid, which was then separated by Chiral-HPLC to afford N-(1-((S)-morpholin-2-ylmethyl)-1H-pyrazol-4-yl)-4-(4-(5-((R)-1-phenylethyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-amine as a white solid (15.4 mg, 17%).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-17e7dabfd6054eb8ba107fca4510a374
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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