4-Methylmorpholine → HCID 19965297, compound

HRID 977158Notes

Reaction equation

HRID 977158 reaction equation
[C:1]([C:3]1[C:4]2[N:5]([CH:9]=[C:10]([C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27]C)=[O:25].OC1C2N=NNC=2C=CC=1.CN1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C.O>[C:1]([C:3]1[C:4]2[N:5]([CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([NH:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:18])=[CH:19][CH:20]=3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 419889Ethyl 3-aminopropanoateHCID 19965292HCID 19965292, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 19965297HCID 19965297, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.0 g Of 4-(8-cyanoimidazo[1,2-a]pyridin-2-yl)benzoic acid and 2.14 g of ethyl 3-aminopropionate in 40 ml of DMF are stirred in the presence of 2.28 g of hydroxybenzotriazole, 3.0 g of N-methylmorpholine and 2.9 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide at room temperature for 4 h. After addition of 400 ml of water, the precipitate is filtered off with suction and washed successively with dilute bicarbonate solution and water. Methyl 3-[4-(8-cyanoimidazo[1,2-a]pyridin-2-yl)benzamido]propionate, m.p 201-204° is obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. washwashed successively with dilute bicarbonate solution and water

Sources & evidence

ORD record
ord-c40ca525c90242819792745a4ca17b1e
Source dataset
uspto-grants-1997_03
Patent number
US05614531

Reaction notes

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