Acetic Acid → HCID 178432040, compound

HRID 1519206Notes

Reaction equation

HRID 1519206 reaction equation
[NH2:1][C:2]1[C:23]([NH2:24])=[CH:22][C:5]2[CH2:6][C@@H:7]3[C:12]([CH3:14])([CH3:13])[C@:11]([CH3:15])([C:4]=2[CH:3]=1)[CH2:10][CH2:9][N:8]3[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18].[C:25](O)(=O)[CH3:26]>>[F:19][C:17]([F:20])([F:18])[C:16]([N:8]1[CH2:9][CH2:10][C@:11]2([CH3:15])[C:12]([CH3:13])([CH3:14])[C@H:7]1[CH2:6][C:5]1[CH:22]=[C:23]3[N:24]=[C:25]([CH3:26])[NH:1][C:2]3=[CH:3][C:4]=12)=[O:21]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 58123670HCID 58123670, compound

Product 1

HCID 178432040HCID 178432040, compound

Conditions

Temperature
130 °C

Procedure

1-[(2R,6S)-8,9-Diamino-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (600 mg) dissolved in glacial acetic acid is stirred at 130° C. for 3 h. After cooling to ambient temperature, the solution is concentrated under reduced pressure and the residue is taken up in ethyl acetate. The organic solution is washed with aqueous K2CO3 solution and brine and dried (MgSO4). The solvent is removed under reduced pressure to give the crude title compound as a foam-like solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe solution is concentrated under reduced pressure
  3. washThe organic solution is washed with aqueous K2CO3 solution and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-89035b5842cb44839b7579006c93aea8
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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