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

HRID 522662Notes

Reaction equation

HRID 522662 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[N:8][C:9]([N:12]3[CH2:17][CH2:16][N:15]([C:18]4[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]5[CH:26]=[N:27][N:28]([CH2:30][C@H:31]6[O:36][CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]6)[CH:29]=5)[N:19]=4)[CH2:14][CH2:13]3)=[N:10][CH:11]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]#[C:5][C:6]2[CH:11]=[N:10][C:9]([N:12]3[CH2:13][CH2:14][N:15]([C:18]4[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]5[CH:26]=[N:27][N:28]([CH2:30][C@H:31]6[O:36][CH2:35][CH2:34][NH:33][CH2:32]6)[CH:29]=5)[N:19]=4)[CH2:16][CH2:17]3)=[N:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118022800(S)-tert-butyl 2-((4-(4-(4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 118023171(S)-4-(4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazin-1-yl)-N-(1-(morpholin-2-ylmethyl)-1H-pyrazol-4-yl)-1,3,5-triazin-2-amineYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-((4-(4-(4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (30 mg, 0.05 mmol) in dichloromethane (2 mL) was dropwise added trifluoroacetic acid (1 mL). The reaction mixture was stirred at room temperature for 0.5 hour and concentrated. The residue was purified by Prep-HPLC to afford (S)-4-(4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazin-1-yl)-N-(1-(morpholin-2-ylmethyl)-1H-pyrazol-4-yl)-1,3,5-triazin-2-amine (14 mg, 57%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-3521b228ba0a42ef8c716ace99946c24
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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