4-Methylmorpholine → rac-N-(2-Amino-2,4-dimethylpentyl)-2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 2275902Notes

Reaction equation

HRID 2275902 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]([CH3:16])=[CH:6][N:5]2[C:17]=1[C:18]([OH:20])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[CH3:50][C:51]([NH2:58])([CH2:54][CH:55]([CH3:57])[CH3:56])[CH2:52][NH2:53]>CN(C=O)C.O.C(O)(C(F)(F)F)=O>[NH2:58][C:51]([CH3:50])([CH2:54][CH:55]([CH3:57])[CH3:56])[CH2:52][NH:53][C:18]([C:17]1[N:5]2[CH:6]=[C:7]([CH3:16])[CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])[C:4]2=[N:3][C:2]=1[CH3:1])=[O:20]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30629272,4-Dimethylpentane-1,2-diamineHCID 867179302,6-Dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 90114247rac-N-(2-Amino-2,4-dimethylpentyl)-2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

175 mg (0.63 mmol) of 2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylic acid Example 252A were initially charged in DMF (2.2 ml), 214 mg (0.67 mmol) of TBTU, 0.28 ml (2.53 mmol) of 4-methylmorpholine and 91 mg (0.70 mmol) of rac-2,4-dimethylpentane-1,2-diamine were added and the reaction mixture stirred at RT overnight. The mixture was diluted with water/TFA and purified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA). After concentration, saturated aqueous sodium bicarbonate solution was added to the residue and the mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered off and concentrated. This gave 225 mg (90% of theory, purity 98%) of the target compound.

Workup

  1. custompurified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA)
  2. concentrationAfter concentration, saturated aqueous sodium bicarbonate solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered off
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ae1f4ecca0142faacdeb42f0bdc855e
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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