Dimethylamine → 3-[3-(5-Dimethylaminomethyl-[1,2,3] triazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

HRID 1266762Notes

Reaction equation

HRID 1266762 reaction equation
CO[C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:14]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:13][N:12]=[N:11]2)[CH:5]=1.N(C1C=C(C=CC=1)C(OC)=O)=[N+]=[N-].O=S(Cl)Cl.CNC.[C:40]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])(=[O:42])[CH3:41].[Li]>C1COCC1>[C:44]([O:43][C:40](=[O:42])[CH2:41][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:14]([CH2:15][N:16]([CH3:17])[CH3:18])=[CH:13][N:12]=[N:11]2)[CH:5]=1)=[O:19])([CH3:47])([CH3:46])[CH3:45]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 11240787Methyl 3-azidobenzoateHCID 696887303-(5-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-benzoic acid methyl esterHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 696876673-[3-(5-Dimethylaminomethyl-[1,2,3] triazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 3-(5-dimethylaminomethyl-[1,2,3]triazol-1-yl)-benzoic acid methyl ester [prepared from methyl 3-azidobenzoate following the synthetic steps i.) to iii.) as described in the preparation of Example K5 and reacting the obtained product with SOCl2 in THF at 0 to 23° C. for 1 h, followed by addition of dimethylamine (7.9 M in H2O) and stirring at 23 to 70° C. for 1 h.] (2.14 g, 8.22 mmol) by treatment with lithium tert.-butyl acetate according to general procedure K (method b). Obtained as a yellow oil (2.90 g).

Workup

  1. customat 0 to 23° C.
  2. customfor 1 h

Sources & evidence

ORD record
ord-c8116d59e87d48b1821cdc84b92c99b2
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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