Trifluoroacetic acid → 1-(4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(piperazin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea

HRID 707126Notes

Reaction equation

HRID 707126 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)=[O:23])=[CH:17][CH:16]=3)[N:12]=[C:11]([N:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)[N:10]=1)[CH2:2]2.FC(F)(F)C(O)=O>ClCCl>[CH:5]12[O:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:9]1[N:10]=[C:11]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[N:12]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)=[O:23])=[CH:19][CH:20]=3)[N:14]=1)[CH2:4]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44548641Tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-pyridin-4-ylureido)phenyl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 445486421-(4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(piperazin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-pyridin-4-ylureido)phenyl)-1,3,5-triazin-2-yl)piperazine-1-carboxylate (approx 1.4 mmol) was taken up in dichloromethane (20 mL) and treated with trifluoroacetic acid (5 mL). The mixture was concentrated under reduced the pressure. To the residue was added diethyl ether to give the title compound as a solid di-TFA salt, which was collected by filtration and dried under house vacuum; MS (ES+) 488.1 (M+H)+

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added diethyl ether

Sources & evidence

ORD record
ord-350f6858807c4f7595c7e7c6cc044ebf
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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