4-Methylmorpholine → HCID 15295423, compound

HRID 977157Notes

Reaction equation

HRID 977157 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[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]=[C:5]2[CH:4]=1)#[N:2].[C:21]([O:25][C:26](=[O:30])[CH2:27][CH2:28][NH2:29])([CH3:24])([CH3:23])[CH3:22].CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C=O)C.ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([NH:29][CH2:28][CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:30])=[O:18])=[CH:19][CH:20]=3)[N:11]=[C:5]2[CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4192171tert-Butyl 3-aminopropanoateHCID 15295421HCID 15295421, compound

Product 1

HCID 15295423HCID 15295423, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6.6 g of 4-(7-cyanoimidazo[1,2-a]pyridin-2-yl)benzoic acid [obtainable as in Example 5]in 100 ml of dichloromethane and 25 ml of DMF are stirred with 4.5 g of β-alanine tert-butyl ester in the presence of 5.25 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide and 6 ml of N-methylmorpholine at room temperature for 20 h. This is followed by extraction 3-4 times with 30 ml of water each time, evaporation and the customary working-up. Tert-butyl 3-[4-(7-cyanoimidazo[1,2-a]pyridin-2-yl)benzamido]propionate is obtained, m.p. 212° (decomposition).

Workup

  1. extractionThis is followed by extraction 3-4 times with 30 ml of water
  2. customeach time, evaporation

Sources & evidence

ORD record
ord-71b49ca01be64db38a8cc2e683b2bffd
Source dataset
uspto-grants-1997_03
Patent number
US05614531

Reaction notes

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