Potassium Carbonate → HCID 59300922, compound

HRID 2235392Notes

Reaction equation

HRID 2235392 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.Cl[CH2:22][C:23]1[N:24]=[CH:25][S:26][CH:27]=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]([CH2:22][C:23]1[N:24]=[CH:25][S:26][CH:27]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochlorideHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300922HCID 59300922, compoundYield 77%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (3.62 g) is alkylated using 4-chloromethyl-thiazole hydrochloride (2.62 g; 15.4 mmol) and K2CO3 (4.41 g; 31.2 mmol) at 50° C. for 3 days. After aqueous work-up and purification by chromatography (SiO2; cyclohexan/EtOAc gradient) the pure material (3.80 g) is de-acetylated in MeOH (100 ml) using DBU (1.6 ml) at 70° C. in 1.5 h. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-thiazol-4-ylmethyl-1,3-dihydro-indol-2-one (3,37 g) is obtained and used without further purification.

Workup

  1. customat 50° C.
  2. customfor 3 days
  3. customAfter aqueous work-up and purification by chromatography (SiO2; cyclohexan/EtOAc gradient) the pure material (3.80 g)
  4. customat 70° C.
  5. customin 1.5 h

Sources & evidence

ORD record
ord-884a9c39125548c6ad14e2705899c1e8
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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