2,6-Lutidine → HCID 10480310, compound

HRID 720523Notes

Reaction equation

HRID 720523 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC)(OC)OC.Br[CH2:17][C:18]([C:20]1[N:21]=[C:22]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[S:23][CH:24]=1)=O.[N:34]1[C:39](C)=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:41].[CH3:42][C:43]#N.[OH2:45]>CN(C)C=O>[CH2:39]([NH:34][C:35]([C:41]1[CH:17]=[C:18]([C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:8]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:42]=1[CH3:43])=[O:45])[CH2:38][CH2:37][CH3:36]

Participants

7

Reactant 5

HCID 79372,6-LutidineHCID 9005Trimethyl orthoformateHCID 76688CyclohexanemethylamineHCID 11858641HCID 11858641, compoundHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 10480310HCID 10480310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 180 mg of the previous crude material in 5 ml of dimethylformamide was added 0.15 ml of cyclohexylmethylamine together with 0.13 ml of trimethyl orthoformate and the reaction mixture was stirred for 24 hours at room temperature. After such time, 260 mg of 2-bromo-1-[2-(4-nitro-phenyl)-thiazol-4-yl]-ethanone was added together with 0.14 ml of 2,6-lutidine and the reaction mixture was stirred for another 24 hours at room temperature. After such time, 5 ml of a MeCN—H2O (1:1) solution is added to the reaction mixture, the precipitate is filtrated and washed with MeCN—H2O (1:1) and isopropylether to yield 264 mg of the title compound as a yellow solid, mp=184–187° C., MS (ISP) 481.3 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for another 24 hours at room temperature
  2. filtrationthe precipitate is filtrated
  3. washwashed with MeCN—H2O (1:1) and isopropylether

Sources & evidence

ORD record
ord-6c07e17b166a409598e13e80488dac3a
Source dataset
uspto-grants-2006_11
Patent number
US07135488B2

Reaction notes

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