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Ammonium Chloride → N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-thiopyran-4-amine-1,1-dioxide hydrochloride

HRID 2171826
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HRID 2171826 반응식
CS(O[CH2:6][C:7]1[C:8]2[CH:16]=[C:15]([CH:17]3[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]3)[S:14][C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)(=O)=O.CCN(C(C)C)C(C)C.[S:34]1(=[O:42])(=[O:41])[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]1.[NH4+].[Cl-:44]>CN(C=O)C>[ClH:44].[CH3:23][C:20]1([CH3:24])[CH2:21][CH2:22][CH:17]([C:15]2[S:14][C:9]3[N:10]=[C:11]([CH3:13])[N:12]=[C:7]([CH2:6][NH:40][CH:37]4[CH2:38][CH2:39][S:34](=[O:42])(=[O:41])[CH2:35][CH2:36]4)[C:8]=3[CH:16]=2)[CH2:18][CH2:19]1
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참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 4188082H-Thiopyran-4-amine, tetrahydro-, 1,1-dioxideHCID 118023751[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate

생성물 1

HCID 118023896N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-thiopyran-4-amine-1,1-dioxide hydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (200 mg), DIPEA (139 μL), and DMF (3.0 mL) was added tetrahydro-2H-thiopyran-4-amine-1,1-dioxide (97 mg), followed by stirring at room temperature for 4 hours. To the reaction mixture was added a saturated aqueous NH4Cl solution, followed by extraction with EtOAc. The organic layer was washed sequentially with water and brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column and dissolved in EtOAc, and 4 M HCl/EtOAc (137 μL) was added dropwise. The precipitate was collected by filtration and then dried to obtain N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-thiopyran-4-amine-1,1-dioxide hydrochloride (165 mg).

후처리

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column
  6. dissolutiondissolved in EtOAc
  7. addition4 M HCl/EtOAc (137 μL) was added dropwise
  8. filtrationThe precipitate was collected by filtration
  9. customdried

출처 및 근거

ORD 기록
ord-97ac3c20b7f2463e8493a1e353283fd7
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051339B2

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