Isobutylamine → Methyl 2''-{[(4-fluorophenyl)methyl]oxy}-5-{[(2-methylpropyl)amino]carbonyl}-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-3-carboxylate

HRID 269563

Reaction equation

HRID 269563 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[C:20]2[C:21]([C:26]3[CH:31]=[C:30]([C:32]([O:34]C)=O)[CH:29]=[C:28]([C:36]([OH:38])=[O:37])[CH:27]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1.[CH3:39]N1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCC(N=C=N)C.[CH2:69]([NH2:73])[CH:70]([CH3:72])[CH3:71]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][C:11]=2[C:20]2[C:21]([C:26]3[CH:31]=[C:30]([C:32]([NH:73][CH2:69][CH:70]([CH3:72])[CH3:71])=[O:34])[CH:29]=[C:28]([C:36]([O:38][CH3:39])=[O:37])[CH:27]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6558IsobutylamineHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 587310142''-{[(4-Fluorophenyl)methyl]oxy}-5-[(methyloxy)carbonyl]-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-3-carboxylic acid

Product 1

HCID 58731015Methyl 2''-{[(4-fluorophenyl)methyl]oxy}-5-{[(2-methylpropyl)amino]carbonyl}-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-3-carboxylateYield 51.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2″-{[(4-fluorophenyl)methyl]oxy}-5-[(methyloxy)carbonyl]-5″-(trifluoromethyl)-1,1′:2′,1″-terphenyl-3-carboxylic acid (90 mg, 0.17 mmol), 4-methylmorpholine (34 mg, 45 μl, 0.34 mmol), 1-hydroxybenzotriazole hydrate (30 mg, 0.2 mmol), 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (38 mg, 0.2 mmol), and isobutylamine (25 mg, 34 ul, 0.34 mmol) in dichloromethane (3 ml) was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (10 ml), then washed with saturated NaHCO3, 2M HCl, water and brine. The organic phase was dried and evaporated. The residue was purified by chromatography in ethyl acetate/hexane (1:9-1:4) to give the title compound as a colourless solid (51 mg, 50%). LCMS: Rt=4.10 min. [M+H] 580

Workup

  1. washwashed with saturated NaHCO3, 2M HCl, water and brine
  2. customThe organic phase was dried
  3. customevaporated
  4. customThe residue was purified by chromatography in ethyl acetate/hexane (1:9-1:4)

Sources & evidence

ORD record
ord-4047a240d5c644808cfa34e5e1c68e3f
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

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