1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

HRID 1775506Notes

Reaction equation

HRID 1775506 reaction equation
C[C:2]1([CH3:20])[CH2:15][N:14]2[C:5](=NC3C([C:13]2=O)=CC=C(C(O)=O)C=3)[CH2:4][CH2:3]1.[OH:21][NH:22][C:23](=[NH:30])C1C=CC=CN=1.CC[N:33]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:4]1[CH:3]2[CH:2]([C:20]3[O:21][N:22]=[C:23]([NH2:30])[N:33]=3)[CH2:15][N:14]([CH2:13]2)[CH2:5]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 711122258,8-dimethyl-11-oxo-7,8,9,11-tetrahydro-6H-pyrido[2,1-b]quinazoline-3-carboxylic acidHCID 178513306HCID 178513306, compound

Product 1

HCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of an acid (e.g., 8,8-dimethyl-11-oxo-7,8,9,11-tetrahydro-6H-pyrido[2,1-b]quinazoline-3-carboxylic acid, 1 equiv), N-hydroxypicolinimidamide (1.5 equiv), EDCI (1.5 equiv) and HOBt (1.5 equiv) in DMF was stirred at 80° C. overnight. The reaction was cooled to room temperature, then the reaction mixture was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude residue was purified by preparative chromatography to give the desired oxadiazole-containing product (e.g., 8,8-dimethyl-3-(3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl)-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude residue was purified by preparative chromatography

Sources & evidence

ORD record
ord-f69aaea2940d4d5e9d2c2cc08f3199b5
Source dataset
uspto-grants-2016_02
Patent number
US09260452B2

Reaction notes

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