HCID 58204043, compound → HCID 58204142, compound

HRID 1190346Notes

Reaction equation

HRID 1190346 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([NH:28]CC5C=CC(OC)=CC=5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([NH2:28])[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1

Participants

3

Reactant 1

HCID 58204043HCID 58204043, compound

Product 1

HCID 58204142HCID 58204142, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulen-9-yl}-(4-methoxy-benzyl)-amine (1.2 g, 2.3 mmol) was dissolved in TFA (20 mL). The reaction mixture was stirred at 80° C. for 2 h. The reaction mixture was concentrated in vacuo, and dissolved in DCM (30 mL). The organic layer was washed by water, dried by Na2SO4, concentrated in vacuo, and separated by preparative TLC (DCM/EtOAc=4:1) to give 134 (800 mg, yield: 87%) 1H NMR (D2O, 400 MHz): δ8.05 (s, 2H), 7.05 (d, J=8.8 Hz, 1H), 7.23 (t, J=2.0 Hz, 1H), 7.14 (s, 1H), 6.99-6.97 (m, 3H), 6.51 (d, J=8.8 Hz, 1H). LC-MS (ESI): m/z=398 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in DCM (30 mL)
  3. washThe organic layer was washed by water
  4. dry with materialdried by Na2SO4
  5. concentrationconcentrated in vacuo
  6. customseparated by preparative TLC (DCM/EtOAc=4:1)

Sources & evidence

ORD record
ord-967e8dbfb94648bcaca7827032d04217
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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