2-Thiophenecarbonyl chloride → HCID 68406816, 화합물

HRID 1713968노트

반응식

HRID 1713968 반응식
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([Cl:10])=[CH:8][CH:9]=1)=O.[N:11]1([CH2:17][CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[S:22])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)C(C)C)(C)C.[S:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38](Cl)=[O:39]>C(O)C>[Cl:10][C:7]1[S:6][C:5]([C:3]2[N:23]=[C:21]([N:20]([CH2:19][CH2:18][CH2:17][N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:38]([C:34]3[S:33][CH:37]=[CH:36][CH:35]=3)=[O:39])[S:22][CH:2]=2)=[CH:9][CH:8]=1

참가 물질

6

반응물 4

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 20636342-(Bromoacetyl)-5-chlorothiopheneHCID 2760135N-[3-(4-Morpholinyl)propyl]thiourea

생성물 1

HCID 68406816HCID 68406816, 화합물수율 44.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-bromo-1-(5-chloro-thiophen-2-yl)-ethanone (72 mg, 0.3 mmol) and (3-morpholin-4-yl-propyl)-thiourea (61 mg, 0.3 mmol) in dry ethanol (3 ml) was heated at reflux for 10 min, cooled to room temperature, and concentrated in vacuo. The resulting residue was suspended in dichloromethane (3 mL) followed by the addition of N,N-diisopropylethylamine (105 μL, 0.6 mmol) and thiophene-2-carbonyl chloride (34 μL, 0.32 mmol). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (1.5 mL) and subjected to HPLC purification (Method Y). The resulting free amine was dissolved in MeOH (1 mL) and 1M HCl/ether (50 mL) was added. The precipitate was filtered and dried in vacuo to provide the title compound (61 mg) as an yellow solid as the hydrochloride salt. LC/MS (ESI) m/z 453.9 [M+H]. HPLC retention time (Method A)=2.93 min.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 10 min
  3. concentrationconcentrated in vacuo
  4. temperatureThe reaction mixture was maintained at room temperature overnight
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting residue was dissolved in DMSO (1.5 mL)
  7. customsubjected to HPLC purification (Method Y)
  8. dissolutionThe resulting free amine was dissolved in MeOH (1 mL)
  9. addition1M HCl/ether (50 mL) was added
  10. filtrationThe precipitate was filtered
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-4460acbe5da34d64862db750a6914e1e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795290B2

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