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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
Notes
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Reaction equation

HRID 2385664 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 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)-amineYield 61.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent
HCID 6344DichloromethaneSolvent
HCID 516892Sodium BicarbonateSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-3e50f5ead2764e4a96a26af9ec1603ae
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263633B2

Reaction notes

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