Triethylamine → HCID 86751343, compound

HRID 1379220Notes

Reaction equation

HRID 1379220 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[CH:2]=1.C(N(CC)CC)C.C1(C(Cl)=O)C2C(=CC=CC=2)C=CC=1.[F:32][C:33]([F:62])([F:61])[C:34]1[CH:35]=[C:36]([CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=1)[C:37]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][C@@H:40]1[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[C:48]([CH3:53])[CH:47]=1)=[O:38]>ClCCl.O>[F:62][C:33]([F:32])([F:61])[C:34]1[CH:35]=[C:36]([CH:54]=[C:55]([C:57]([F:58])([F:59])[F:60])[CH:56]=1)[C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:9](=[O:11])/[CH:8]=[CH:7]/[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:41][C@@H:40]1[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[C:48]([CH3:53])[CH:47]=1)=[O:38]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 701461-Naphthalenecarbonyl chlorideHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 86751344HCID 86751344, compound

Product 1

HCID 86751343HCID 86751343, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred mixture of trans-3-(3-pyridyl)acrylic acid (100 mg) and triethylamine (0.19 ml) in dichloromethane (10 ml) was added 1-naphthoyl chloride (0.1 ml) at -15° C. After stirring for 30 minutes, a solution of (2S)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (300 mg) in dichloromethane (10 ml) was added at -15° C. and the resulting mixture was stirred for 30 minutes at the same temperature and then for 1 hour at room temperature. Dichloromethane and water were added to the reaction mixture and the organic layer was separated, washed successively with aqueous saturated sodium bicarbonate solution, water, 0.5N hydrochloric acid and brine, and dried over magnesium sulfate. After evaporation of the solvent in vacuo, the residue was purified on a silica gel column (20 g) eluting with a mixture of dichloromethane and methanol (100:2) to give (2S)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethyl benzyl)-4-[3-(3-pyridyl)-trans-acryloyl]piperazine (0.34 g).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes at the same temperature
  2. waitfor 1 hour at room temperature
  3. customthe organic layer was separated
  4. washwashed successively with aqueous saturated sodium bicarbonate solution, water, 0.5N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent in vacuo
  7. customthe residue was purified on a silica gel column (20 g)
  8. washeluting with a mixture of dichloromethane and methanol (100:2)

Sources & evidence

ORD record
ord-f0e0924c396649ff82838e27808830cd
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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