Diisopropylethylamine → HCID 57666072, compound

HRID 889728Notes

Reaction equation

HRID 889728 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[F:33][C:34]([F:45])([F:44])[O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1.C(N(C(C)C)CC)(C)C>CC#N.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:40][C:39]3[CH:42]=[CH:43][C:36]([O:35][C:34]([F:33])([F:44])[F:45])=[CH:37][CH:38]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 57666072HCID 57666072, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 33b 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (60.8 mg, 0.136 mmol) in CH3CN (5 ml) was added 4-Trifluoromethoxybenzylbromide) (33 μl, 0.20 mmol) and diisopropylethylamine (47 μl, 0.27 mmol). The reaction was microwaved at 130° C. for 10 minutes, then diluted with EtOAc and washed with brine, sat. NaHCO3, and brine, dried and filtered. Purification by silica gel chromatography (Isco) gave the desired product as a clear oil, (69.7 mg, 83%). Calcd for C34H37F6NO3 (M+H) 621.65, Found 622.3

Workup

  1. customThe reaction was microwaved at 130° C. for 10 minutes
  2. washwashed with brine, sat. NaHCO3, and brine
  3. customdried
  4. filtrationfiltered
  5. customPurification by silica gel chromatography (Isco)

Sources & evidence

ORD record
ord-24273678c15e47318a6f74322c53dbf2
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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