Hydrochloric Acid → trans-N-(8-Amino-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16166Notes

Reaction equation

HRID 16166 reaction equation
Cl.O.O.Cl[Sn]Cl.[Cl:7][C:8]1[C:33]([N+:34]([O-])=O)=[CH:32][C:11]2[O:12][C:13]3[CH:31]=[CH:30][CH:29]=[CH:28][C:14]=3[C@@H:15]3[C@H:20]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH2:19][CH2:18][CH2:17][N:16]3[C:10]=2[CH:9]=1>C(O)C>[NH2:34][C:33]1[C:8]([Cl:7])=[CH:9][C:10]2[N:16]3[CH2:17][CH2:18][CH2:19][C@@H:20]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[C@H:15]3[C:14]3[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=3[O:12][C:11]=2[CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 86599874trans-N-(7-chloro-8-nitro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86599875trans-N-(8-Amino-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

80 μL 36% HCl and SnCl2.2H2O (600 mg, 2.66 mmol) were added trans-N-(7-chloro-8-nitro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (215 mg, 0.49 mmol) in 10 mL of ethanol. The resulting mixture was stirred at 60° C. for 18 h. After cooling the mixture was evaporated and dissolved in ethyl acetate. Aq. sodium bicarbonate was added to the solution (Sn salts were formed) followed by decalite and the mixture was filtered. The filtrate was extracted with ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and evaporated to give the title compound (194 mg, 82%). Data: (m/z)=413 (M+H)+.

Workup

  1. temperatureAfter cooling the mixture
  2. customwas evaporated
  3. dissolutiondissolved in ethyl acetate
  4. additionAq. sodium bicarbonate was added to the solution (Sn salts were formed)
  5. filtrationthe mixture was filtered
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washthe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-d751b0acdeec474987caece0e86f4a50
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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