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Diisopropyl Ether → 8-[(2,6-difluorobenzyl)oxy]-N-[2-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 923516
ノート
印刷プレビュー

反応式

HRID 923516 の反応式
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.FC(F)(F)C(O)=O.[NH2:31][C:32]([C:36]1[O:37][C:38]([CH2:41][CH3:42])=[N:39][N:40]=1)([CH3:35])[CH2:33][OH:34].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.C(OC(C)C)(C)C>C(OCC)(=O)C.O.CN(C=O)C>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:31][C:32]([C:36]3[O:37][C:38]([CH2:41][CH3:42])=[N:39][N:40]=3)([CH3:35])[CH2:33][OH:34])=[O:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 6

HCID 7914Diisopropyl EtherHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 1183087322-Amino-2-(5-ethyl-1,3,4-oxadiazol-2-yl)propan-1-ol trifluoroacetate

生成物 1

HCID 1183087588-[(2,6-difluorobenzyl)oxy]-N-[2-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide収率 24.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 165 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid, 160 mg of 2-amino-2-(5-ethyl-1,3,4-oxadiazol-2-yl)propan-1-ol trifluoroacetate, 90 mg of 1-hydroxybenzotriazole, 0.35 ml of diisopropylethylamine, and 4 ml of DMF was added 130 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. To the obtained crude product were added ethyl acetate and diisopropyl ether, and the insoluble materials were collected by filtration, and dried under reduced pressure to obtain 59 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[2-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. customTo the obtained crude product
  7. filtrationthe insoluble materials were collected by filtration
  8. customdried under reduced pressure

出典と根拠

ORDレコード
ord-58de55175c024a83937d94d72071cada
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278968B2

反応ノート

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