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

HRID 1775506노트

반응식

HRID 1775506 반응식
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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f69aaea2940d4d5e9d2c2cc08f3199b5
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260452B2

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