Potassium Carbonate → HCID 59301000, compound

HRID 2235394Notes

Reaction equation

HRID 2235394 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].Cl[CH2:21][C:22]1[O:26][N:25]=[C:24]([CH3:27])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:21][C:22]1[O:26][N:25]=[C:24]([CH3:27])[CH:23]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 71314965-(Chloromethyl)-3-methyl-1,2-oxazoleHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59301000HCID 59301000, compoundYield 25.8%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (3 g) is alkylated using 5-chloromethyl-3-methyl-isoxazole (1.65 g; 12.5 mmol) and K2CO3 (3,3 g; 23.9 mmol) at RT for 3 days. After aqueous work-up and purification by RP chromatography the pure material (1.07 g) is de-acetylated in MeOH (50 ml) using DBU (220 μl) at 60° C. in 18 h. After aqueous work-up 5-amino-3,3-dimethyl-1-(3-methyl-isoxazol-5-ylmethyl)-6-nitro-1,3-dihydro-indol-2-one (0.93 g) is obtained and used without further purification.

Workup

  1. customat RT
  2. customfor 3 days
  3. customAfter aqueous work-up and purification by RP chromatography the pure material (1.07 g)
  4. customat 60° C.
  5. customin 18 h

Sources & evidence

ORD record
ord-cebe2288cda24a5b9cd893866cca7789
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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