2-Thiophenecarbonyl chloride → HCID 68406167, 화합물

HRID 1713971노트

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HRID 1713971 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])=O.[N:15]1([CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH2:27])=[S:26])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](Cl)=[O:43]>O1CCOCC1>[CH3:14][O:13][C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[C:3]1[N:27]=[C:25]([N:24]([CH2:23][CH2:22][CH2:21][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[C:42]([C:38]2[S:37][CH:41]=[CH:40][CH:39]=2)=[O:43])[S:26][CH:2]=1

참가 물질

6

반응물 4

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 986832-Bromo-1-(2,4-dimethoxyphenyl)ethanoneHCID 2760135N-[3-(4-Morpholinyl)propyl]thiourea

생성물 1

HCID 68406167HCID 68406167, 화합물수율 72.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of 2-bromo-2′,4′-dimethoxyacetophenone (156 mg, 0.6 mmol) and (3-morpholin-4-yl-propyl)-thiourea (122 mg, 0.6 mmol) in dry dioxane (5 ml) was heated at 80° C. for 2 h, cooled to room temperature, and concentrated in vacuo. The resulting residue was suspended in dichloromethane (5 mL) followed by the addition of N,N-diisopropylethylamine (209 μL, 1.2 mmol) and thiophene-2-carbonyl chloride (96 μL, 0.9 mmol). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (2.5 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 (207 mg) as an yellow solid as the hydrochloride salt. LC/MS (ESI) m/z 474.3 [M+H]. HPLC retention time (Method A)=2.81 min.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. temperatureThe reaction mixture was maintained at room temperature overnight
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in DMSO (2.5 mL)
  6. customsubjected to HPLC purification (Method Y)
  7. dissolutionThe resulting free amine was dissolved in MeOH (1 mL)
  8. addition1M HCl/ether (50 mL) was added
  9. filtrationThe precipitate was filtered
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-e6276033429d4d09be7db005aca18d2c
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795290B2

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