Trifluoroacetic acid → N-(4-amino-5-methyl-3-oxohexyl)-2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamide

HRID 1782182Notes

Reaction equation

HRID 1782182 reaction equation
FC(F)(F)C(O)=O.[Cl:8][CH:9]([Cl:48])[C:10]([N:12]([CH2:32][CH2:33][C:34](=[O:47])[CH:35]([NH:39]C(=O)OC(C)(C)C)[CH:36]([CH3:38])[CH3:37])[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[CH:20]=2)[CH:14]=1)=[O:11]>C(Cl)Cl>[NH2:39][CH:35]([CH:36]([CH3:38])[CH3:37])[C:34](=[O:47])[CH2:33][CH2:32][N:12]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=3[Cl:30])[CH:20]=2)[CH:14]=1)[C:10](=[O:11])[CH:9]([Cl:48])[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57588429tert-butyl 6-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-2-methyl-4-oxohexan-3-ylcarbamate

Product 1

HCID 12002082N-(4-amino-5-methyl-3-oxohexyl)-2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of tert-butyl 6-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-2-methyl-4-oxohexan-3-ylcarbamate (185 mg, 0.29 mmol) in methylene chloride (2 mL) at 0° C. The resulting mixture was allowed to stir at 0° C. for 2 hours, then concentrated under reduced pressure. The residue was dissolved in methylene chloride (2 mL) and concentrated under reduced pressure, twice more. Then lyophilized to produce N-(4-amino-5-methyl-3-oxohexyl)-2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamide (Cpd. No. 3, lot 2, 150 mg) as a light orange solid. 1H NMR (CD3OD): 8.90 (d, 1H), 8.28 (s, 1H), 7.80-7.75 (m, 1H), 7.65-7.55 (m, 3H), 7.38 (s, 1H), 6.62 (s, 1H), 4.38-4.11 (m, 3H), 3.19-3.08 (m, 2H), 2.55-2.41 (m, 1H), 1.15 (d, 3H), 0.90 ppm (d, 3H). MW=544 confirmed by LC-MS, tr=10.55 min (Method Y) MH+=542-546.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride (2 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e815ee4cdbf4333954884d6a3a5fa5d
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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