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1,2-Dichloroethane → (+)-(6-(Azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)(morpholino)methanone

HRID 1868488
ノート
印刷プレビュー

反応式

HRID 1868488 の反応式
[N:1]([CH2:4][C:5]1[C:6]([CH3:25])=[N:7][C:8]2[N:9]([CH:19]=[C:20]([C:22]([OH:24])=O)[N:21]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[N+:2]=[N-:3].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>C1COCC1>[N:1]([CH2:4][C:5]1[C:6]([CH3:25])=[N:7][C:8]2[N:9]([CH:19]=[C:20]([C:22]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:24])[N:21]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[N+:2]=[N-:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 46901748(+)-6-(Azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

生成物 1

HCID 57982555(+)-(6-(Azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)(morpholino)methanone
収率 99.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (+)-6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (150 mg, 0.40 mmol) in THF (10 mL) was added morpholine (52 mg, 0.60 mmol), HOAt (81 mg, 0.60 mmol), EDC (114 mg, 0.60 mmol) and iPr2NEt (103 mg, 0.80 mmol). The reaction was kept at room temperature for 2 h and was concentrated under reduced pressure. The residue was diluted with EtOAc and the organic layer was washed with 1N HCl, 1N NaOH and brine prior to drying over anhydrous MgSO4. Filtration and concentration under reduced pressure afforded (+)-(6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)(morpholino)methanone (177 mg, 100% crude yield) as a clear glass.

後処理

  1. concentrationwas concentrated under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washthe organic layer was washed with 1N HCl, 1N NaOH and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-355ab0eac76d42468945097155b17f96
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07635699B2

反応ノート

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