4-Methylmorpholine → HCID 90114235, compound

HRID 2275899Notes

Reaction equation

HRID 2275899 reaction equation
[CH3:1][C:2]([NH2:8])([CH2:5][CH2:6][CH3:7])[CH2:3][NH2:4].[F:9][C:10]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:11]=1[CH2:12][O:13][C:14]1[C:15]2[N:16]([C:21]([C:25](O)=[O:26])=[C:22]([CH3:24])[N:23]=2)[CH:17]=[C:18]([CH3:20])[CH:19]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C.O.C(O)(C(F)(F)F)=O>[NH2:8][C:2]([CH3:1])([CH2:5][CH2:6][CH3:7])[CH2:3][NH:4][C:25]([C:21]1[N:16]2[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([O:13][CH2:12][C:11]3[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:10]=3[F:9])[C:15]2=[N:23][C:22]=1[CH3:24])=[O:26]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11170953100868-68-6HCID 867178848-[(2,6-Difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 90114235HCID 90114235, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

77 mg (0.66 mmol) of rac-2-methylpentane-1,2-diamine were added to 200 mg (0.60 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid Example 21A, 203 mg (0.63 mmol) of TBTU and 0.27 ml (2.41 mmol) of 4-methylmorpholine in DMF (2.1 ml), and the reaction mixture was 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). The product fraction was concentrated. Saturated aqueous sodium bicarbonate solution was added to the residue, and the mixture was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered off and concentrated. This gave 199 mg (76% of theory, purity 99%) of the target compound.

Workup

  1. custompurified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA)
  2. concentrationThe product fraction was concentrated
  3. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  4. extractionthe mixture was extracted twice with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered off
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-83c101ffb9674bb8a7b17aa8a9c7e12e
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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