Ethanamine, 2,2,2-trifluoro- → HCID 44598517, compound

HRID 1958875Notes

Reaction equation

HRID 1958875 reaction equation
N=C=N.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:34]([F:37])([F:36])[F:35])[O:16][N:15]=[C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:27]([NH:29][CH2:30][C:31](O)=[O:32])=[O:28])=[CH:19][CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1.[F:38][C:39]([F:43])([F:42])[CH2:40][NH2:41]>ClCCl>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:34]([F:36])([F:37])[F:35])[O:16][N:15]=[C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:27]([NH:29][CH2:30][C:31](=[O:32])[NH:41][CH2:40][C:39]([F:43])([F:42])[F:38])=[O:28])=[CH:19][CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 160435CarbodiimideHCID 68512729HCID 68512729, compound2×

Product 1

HCID 44598517HCID 44598517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PS-Carbodiimide (0.53 g, 123 mmol/g, Argonaut Technologies, Inc.) was added to a stirred mixture of N-[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine (i.e. the product of Step D, 510 mg) and 2,2,2-trifluoroethylamine (0.072 mL) in dichloromethane (3 mL) at room temperature. The mixture was stirred at room temperature for 5 h, then filtered and concentrated under reduced pressure. The residue was purified by column chromatography to provide the title compound (99 mg), a compound of this invention, as a white solid. 1H NMR (CDCl3): δ 8.82 (d, 1H), 8.26 (d, 1H), 7.46-7.67 (m, 7H), 7.09 (m, 2H), 4.28 (d, 2H), 4.25 (d, 1H), 3.96 (m, 2H), 3.88 (d, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cd3b185da15e41919546cfe70d9ea9b0
Source dataset
uspto-grants-2013_04
Patent number
US08410153B2

Reaction notes

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