Ethanamine, 2,2,2-trifluoro- → HCID 25113659, compound

HRID 1958878Notes

Reaction equation

HRID 1958878 reaction equation
N=C=N.[F:4][C:5]([F:43])([F:42])[C:6]1[CH:7]=[C:8]([C:16]2([C:38]([F:41])([F:40])[F:39])[O:20][N:19]=[C:18]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([C:31]([NH:33][CH2:34][C:35]([OH:37])=O)=[O:32])=[CH:23][CH:22]=3)[CH2:17]2)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1.[F:44][C:45]([F:49])([F:48])[CH2:46][NH2:47]>ClCCl>[F:4][C:5]([F:42])([F:43])[C:6]1[CH:7]=[C:8]([C:16]2([C:38]([F:40])([F:41])[F:39])[O:20][N:19]=[C:18]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([C:31]([NH:33][CH2:34][C:35](=[O:37])[NH:47][CH2:46][C:45]([F:49])([F:48])[F:44])=[O:32])=[CH:23][CH:22]=3)[CH2:17]2)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 160435CarbodiimideHCID 86646213HCID 86646213, compound2×

Product 1

HCID 25113659HCID 25113659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PS-Carbodiimide (400 mg, 123 mmol/g, Argonaut Technologies, Inc.) was added to a stirred mixture of N-[[4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine (i.e. the product of Step C, 140 mg) and 2,2,2-trifluoroethylamine (0.038 mL) in dichloromethane (3 mL) at room temperature. The mixture was stirred at room temperature overnight, then filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with ethyl acetate/hexanes to provide the title compound (115 mg), a compound of this invention, as a white solid. 1H NMR (CDCl3): δ 8.77 (d, 1H), 8.16 (d, 1H), 8.13 (s, 2H), 8.01 (s, 1H), 7.51-7.60 (m, 3H), 7.46 (t, 1H), 7.42 (d, 1H), 7.33 (d, 1H), 4.31 (d, 1H), 4.23 (d, 2H), 3.83-3.92 (m, 3H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. washeluted with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-58ba82bfc2014327871c051a2db1d985
Source dataset
uspto-grants-2013_04
Patent number
US08410153B2

Reaction notes

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