N,N-Diethylethanamine trihydrofluoride → HCID 178483426, compound

HRID 630378Notes

Reaction equation

HRID 630378 reaction equation
[OH:1][C:2]([C:51]1[S:52][CH:53]=[CH:54][CH:55]=1)([C:46]1[S:47][CH:48]=[CH:49][CH:50]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C@H:25]([O:38][Si](C(C)(C)C)(C)C)[C:26]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]3[C:27]=2[CH:28]=[CH:29][C:30](=[O:37])[NH:31]3)[CH3:13])[CH2:8][CH2:7]1)=[O:4].F.F.F.C(N(CC)CC)C>O1CCCC1.C(Cl)Cl>[OH:1][C:2]([C:46]1[S:47][CH:48]=[CH:49][CH:50]=1)([C:51]1[S:52][CH:53]=[CH:54][CH:55]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C@H:25]([OH:38])[C:26]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]3[C:27]=2[CH:28]=[CH:29][C:30](=[O:37])[NH:31]3)[CH3:13])[CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 178483427HCID 178483427, compound2×

Product 1

HCID 178483426HCID 178483426, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-4-[(9-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}nonyl)(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 7; 0.8 g, 0.13 mmol) in tetrahydrofuran (5.1 mL) was added triethylamine trihydrofluoride (0.14 mL, 0.89 mmol) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 20 hours. The crude reaction was diluted with methylene chloride and the organic layer washed with sodium bicarbonate and brine, dried, filtered and evaporated. The crude product was purified by preparative reversed-phase HPLC (System 1) obtaining the title compound as a colourless solid (61%).

Workup

  1. customThe crude reaction
  2. washthe organic layer washed with sodium bicarbonate and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by preparative reversed-phase HPLC (System 1)

Sources & evidence

ORD record
ord-2462d79ed1d24fcb888c4a57d014edf9
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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