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Ethanamine, 2,2,2-trifluoro- → [2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-(2,2,2-trifluoro-ethyl)-amine

HRID 2385664
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HRID 2385664 반응식
[CH:1]([N:4]1[CH:8]=[N:7][N:6]=[C:5]1[C:9]1[S:10][C:11]2[CH2:12][CH2:13][O:14][C:15]3[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:16]=3[C:17]=2[N:18]=1)([CH3:3])[CH3:2].[F:25][C:26]([F:30])([F:29])[CH2:27][NH2:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(=O)(O)[O-].[Na+].C(Cl)Cl>[CH:1]([N:4]1[CH:8]=[N:7][N:6]=[C:5]1[C:9]1[S:10][C:11]2[CH2:12][CH2:13][O:14][C:15]3[CH:22]=[C:21]([CH2:23][NH:28][CH2:27][C:26]([F:30])([F:29])[F:25])[CH:20]=[CH:19][C:16]=3[C:17]=2[N:18]=1)([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5049666Sodium triacetoxyborohydrideHCID 582037272-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbaldehyde

생성물 1

HCID 58203778[2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-(2,2,2-trifluoro-ethyl)-amine수율 61.5%

시약·촉매·용매 3

HCID 11
1,2-Dichloroethane
용매
HCID 6344Dichloromethane용매
HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbaldehyde (180 mg, 0.53 mmol) in DCE (7 mL+5% AcOH) was added trifluoroethylamine (46 μL, 0.58 mmol) and the mixture was stirred for 30 minutes. Sodium triacetoxyborohydride (134 mg, 0.64 mmol) was added and the solution was stirred under nitrogen for 65 hours. The reaction mixture was diluted with aqueous saturated sodium bicarbonate solution and DCM and the phases were separated. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, 0-5% 2M NH3/MeOH in DCM) to give a colourless oil. The oil was triturated with ether/cyclohexane to give 119 as a grey solid (138 mg, 61%). LCMS: RT=9.52 min, [M+H]+=424. 1H NMR δ (ppm) (DMSO-d6): 8.91 (1 H, s), 8.22 (1 H, d, J=8.10 Hz), 7.09 (1 H, dd, J=8.16, 1.68 Hz), 7.00 (1 H, d, J=1.64 Hz), 5.49-5.39 (1 H, m), 4.33-4.27 (2 H, m), 3.74 (2 H, s), 3.40-3.32 (2 H, m), 3.21-3.09 (2 H, m), 2.92 (1H, s), 1.52 (6H, d, J=6.71 Hz)

후처리

  1. stirringthe solution was stirred under nitrogen for 65 hours
  2. customthe phases were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by flash chromatography (SiO2, 0-5% 2M NH3/MeOH in DCM)
  7. customto give a colourless oil
  8. customThe oil was triturated with ether/cyclohexane

출처 및 근거

ORD 기록
ord-3e50f5ead2764e4a96a26af9ec1603ae
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263633B2

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