Potassium Carbonate → HCID 86719511, compound

HRID 1772273Notes

Reaction equation

HRID 1772273 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:15]=3[CH:16]=2)[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[N+:31]([C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=2)=[CH:36][C:35]=1[C:48]([F:51])([F:50])[F:49])([O-:33])=[O:32]>C(#N)C>[N+:31]([C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]2[CH:42]=[CH:43][C:44]([O:47][CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([CH2:11][C:12]4[O:13][C:14]5[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:15]=5[CH:16]=4)[CH2:7][CH2:6]3)=[O:4])=[CH:45][CH:46]=2)=[CH:36][C:35]=1[C:48]([F:49])([F:50])[F:51])([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86719494HCID 86719494, compoundHCID 86719512HCID 86719512, compound

Product 1

HCID 86719511HCID 86719511, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-1-(4-[[5-(trifluoromethyl)-1-benzofuran-2-yl]methyl]piperazin-1-yl)ethan-1-one (100 mg, 0.28 mmol) in acetonitrile (10 ml) was added potassium carbonate (57.5 mg, 0.42 mmol) and 4-[4-nitro-3-(trifluoromethyl)phenyl]aminophenol (83 mg, 0.28 mmol). The mixture was stirred and heated at 80° C. (oil bath) for 3 hours. The solids were filtered off and the filtrate was concentrated under vacuum to give a residue, which was purified by Prep-TLC with 60% ethyl acetate in petroleum ether to afford 2-(4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]phenoxy)-1-(4-[[5-(trifluoromethyl)-1-benzofuran-2-yl]methyl]piperazin-1-yl)ethan-1-one as a yellow solid (125.8 mg, 73%); (ES, m/z): [M+H]+ 623.20; 1H NMR (400 MHz, CDCl3): δ 8.00 (d, J=8.8 Hz, 1H), 7.86 (s, 1H), 7.60 (m, 2H), 7.14 (overlapping s & d, 3H), 7.00 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.8 Hz, 1H), 6.72 (s, 1H), 6.29 (s, 1H), 4.74 (s, 2H), 3.91-3.53 (m, 6H), 2.60 (br s, 4H).

Workup

  1. filtrationThe solids were filtered off
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto give a residue, which
  4. customwas purified by Prep-TLC with 60% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-aec263527b294032abd597189055cfd3
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

Loading…