Trifluoroacetic acid methylene chloride → (R)-1-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 2099842Notes

Reaction equation

HRID 2099842 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@@H:21]([C:41]3[O:45][N:44]=[C:43]([C:46]4[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=4)[N:42]=3)[CH2:22][C:23]3[CH:31]=[C:30]([CH3:32])[C:29]4[C:25](=[CH:26][N:27](COCC[Si](C)(C)C)[N:28]=4)[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.FC(F)(F)C(O)=O.C(Cl)Cl>>[O:1]=[C:2]1[C:11]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C@@H:21]([C:41]3[O:45][N:44]=[C:43]([C:46]4[CH:47]=[CH:48][C:49]([F:52])=[CH:50][CH:51]=4)[N:42]=3)[CH2:22][C:23]3[CH:24]=[C:25]4[C:29](=[C:30]([CH3:32])[CH:31]=3)[NH:28][N:27]=[CH:26]4)=[O:19])[CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57794682(R)-1-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 57794689(R)-1-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylateYield 65%

Procedure

A stirred solution of (R)-1-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (16.2 mg, 0.0224 mmol) in 1:1 trifluoroacetic acid/methylene chloride 91 mL) was stirred at room temperature for 2 h. Removal of the solvents in vacuo followed by purification using preparative HPLC afforded a tan gum (8.6 mg, 65%). 1H-NMR (CDCl3, 400 MHz) δ 8.22 (s, 1H), 8.12-8.01 (m,2H), 7.80 (s, 1H), 7.76-7.45 (m, 5H), 7.35-7.45 (m, 2H), 7.30 (s,1H), 7.20-7.07 (m,2H), 6.28-6.15 (m,1H), 4.42-4.25 (m,2H), 3.57-3.45 (m,2H) 3.31-2.85 (m, 4H), 2.60 (s,3H), 2.09-1.88 (m,2H), 1.70-1.53 (m,2H). Mass spec. 593.28 (MH+).

Workup

  1. customRemoval of the solvents in vacuo
  2. customfollowed by purification

Sources & evidence

ORD record
ord-50bbb4dde0554e8e99f887df527feed4
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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