Acetone → Isopropyl 3-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)propanoate

HRID 1782196Notes

Reaction equation

HRID 1782196 reaction equation
[I-].[Na+].[C:3](=[O:11])([O:7][CH:8]([CH3:10])[CH3:9])OCCl.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[C:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([NH2:31])[CH:28]=[CH:27][N:26]=2)[O:22][N:21]=1.[CH3:32][C:33](C)=O>>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[C:14]=1[C:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([NH:31][CH2:32][CH2:33][C:3]([O:7][CH:8]([CH3:9])[CH3:10])=[O:11])[CH:28]=[CH:27][N:26]=2)[O:22][N:21]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 14787051Chloromethyl isopropyl carbonateHCID 575883082-(3-(2,6-Dichlorophenyl)isoxazol-5-yl)pyridin-4-amine

Product 1

HCID 69055819Isopropyl 3-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)propanoate

Procedure

Sodium iodide (1.4 g, 9.3 mmol) was added to a solution of chloromethyl isopropyl carbonate (750 mg, 4.8 mmol) in acetone (5 mL). The resulting mixture was stirred at room temperature for 2.5 h, followed by addition of 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine (500 mg, 1.6 mmol). The reaction mixture was then stirred at room temperature for 7 d. The reaction mixture was concentrated under reduced pressure to provide isopropyl 3-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)propanoate, which was carried forward without further purification. 1H NMR (CDCl3): 8.56 (d, 1H), 7.96 (s, 1H), 7.62 (m, 1H), 7.42-7.30 (m, 4H), 7.01 (s, 1H), 6.26 (d, 2H), 5.02 (m, 1H), 1.31 ppm (d, 6H).

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 7 d
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4743145e64694620a48b0d24d78ebb40
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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