N,N-Diethylethanamine trihydrofluoride → HCID 68809005, compound

HRID 730933Notes

Reaction equation

HRID 730933 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH:33][CH2:34][C@H:35]([O:48][Si](C(C)(C)C)(C)C)[C:36]4[CH:45]=[CH:44][C:43]([OH:46])=[C:42]5[C:37]=4[CH:38]=[CH:39][C:40](=[O:47])[NH:41]5)=[CH:27][CH:26]=3)[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F.F.F.C(N(CC)CC)C>C1COCC1.CO>[CH2:1]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[C:18]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH:33][CH2:34][C@H:35]([OH:48])[C:36]4[CH:45]=[CH:44][C:43]([OH:46])=[C:42]5[C:37]=4[CH:38]=[CH:39][C:40](=[O:47])[NH:41]5)=[CH:27][CH:26]=3)[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 68810019HCID 68810019, compound

Product 1

HCID 68809005HCID 68809005, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

N-{2-[4-(3-(3-(N-benzylamino)methylphenyl)-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-tert-butyldimethylsilyloxy-2-(8-hydroxy-2(1H)-quinolinon-5-yl)ethylamine (55 mg, 0.73 mmol) was dissolved in THF/MeOH (5 mL:2 mL). Triethylamine-trihydrofluoride (0.5 mL) was added, and the reaction mixture was stirred at room temperature for 5 h. The solvent was then evaporated, and the residue purified by HPLC to afford N-{2-[4-(3-(3-(N-benzylamino)methylphenyl)-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-hydroxy-2-(8-hydroxy-2(1H)-quinolinon-5-yl)ethylamine (114). m/z: [M+H+] calcd for C40H41N4O4 641.31. found 641.3

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-6404a7638e1b4dafb7269ea5bc5103bb
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

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