Triethylamine → HCID 69506700, compound

HRID 2366696Notes

Reaction equation

HRID 2366696 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:9][CH:8]=[CH:7][CH:6]=2.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22].C(N(CC)CC)C>>[CH2:21]([O:23][CH2:24][C:25]1[N:12]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]2[C:10]3[N:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:22]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 57455388HCID 57455388, compound

Product 1

HCID 69506700HCID 69506700, compoundYield 99.8%

Procedure

Ethyl 4-(3-amino[1,5]naphthyridin-4-ylamino)butanoate (2.5 g, 9.1 mmol, prepared in Parts A and B of Example 37) was treated with ethoxyacetyl chloride (1.02 mL, 10.0 mmol) and cyclized according to a modification of the method described in Part C of Example 37. The reaction with triethylamine (3.8 mL, 27 mmol) was heated at reflux overnight and was complete. Following the work-up procedure, 3.11 g of ethyl 4-(2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanoate were obtained as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight

Sources & evidence

ORD record
ord-246dc7d0c1dc4d4fae5872a0aebad445
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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