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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
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HRID 1868488 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-355ab0eac76d42468945097155b17f96
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07635699B2

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