HCID 18416130, compound → HCID 18416175, compound

HRID 1350169Notes

Reaction equation

HRID 1350169 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[N:8]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH:9]([C:12]([F:15])([F:14])[F:13])[CH2:10][O:11][C:6]=2[CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:22]=[CH:21][C:7]2[N:8]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH:9]([C:12]([F:13])([F:14])[F:15])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 18416130HCID 18416130, compound

Product 1

HCID 18416175HCID 18416175, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (±)-3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine (100 mg, 0.30 mmol) in 1.5 mL ethyl acetate was added 10% Pd—C (42 mg). The reaction mixture was then purged with nitrogen and then purged with hydrogen. A hydrogen balloon was then inserted through a septum into the reaction mixture and allowed to stir for 3 hours at room temperature. The solution was then filtered through a pad of celite and rinsed with ethyl acetate. The solvent was evaporated under reduced pressure to give a crude brown oil which was purified via flash chromatography (2:1 hexanes:EtOAc) to afford 85 mg (93%) (±)-7-amino-3,4-dihydro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine. 1H NMR (400 MHz, CDCl3) 6.68 (d, 1H, J=8.4), 6.32–6.28 (m, 2H), 4.56 (dd, 1H, J=12.0, 0.96), 4.16–4.00 (m, 2H), 3.84–3.69 (m, 2H), 3.60–3.32 (m, 2H).

Workup

  1. customThe reaction mixture was then purged with nitrogen
  2. custompurged with hydrogen
  3. filtrationThe solution was then filtered through a pad of celite
  4. washrinsed with ethyl acetate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give a crude brown oil which
  7. customwas purified via flash chromatography (2:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-a3181382159d44109b5241047f63e726
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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