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

HRID 1775506ノート

反応式

HRID 1775506 の反応式
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

参加物

7

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f69aaea2940d4d5e9d2c2cc08f3199b5
出典データセット
uspto-grants-2016_02
特許番号
US09260452B2

反応ノート

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