Potassium Carbonate → 5-Amino-1-(2,4-dimethyl-thiazol-5-ylmethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one

HRID 2235393Notes

Reaction equation

HRID 2235393 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[S:26][C:25]([CH3:27])=[N:24][C:23]=1[CH3:28].C([O-])([O-])=O.[K+].[K+].C1CCN2C(=NCCC2)CC1>CO>[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[S:26][C:25]([CH3:27])=[N:24][C:23]=1[CH3:28])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 150230585-(Chloromethyl)-2,4-dimethyl-1,3-thiazoleHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 593010275-Amino-1-(2,4-dimethyl-thiazol-5-ylmethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-oneYield 61.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1.77 g) is alkylated using 5-chloromethyl-2,4-dimethyl-thiazole (1.09 g; 6.74 mmol) (Zh. Obshch. Khim. 1956, engl. transl. 3835) and K2CO3 (1.05 g; 7.41 mmol) at 60° C. for 3 days. After aqueous work-up the crude material is de-acetylated in MeOH (70 ml) using DBU (2.2 ml) at reflux. After aqueous work-up 5-amino-1-(2,4-dimethyl-thiazol-5-ylmethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (1.44 g) is obtained and used without further purification.

Workup

  1. customat 60° C.
  2. customfor 3 days
  3. temperatureat reflux

Sources & evidence

ORD record
ord-996dc4457a9b4dea86ece965f80c4808
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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