Acetonitrile → HCID 86750580, compound

HRID 976332Notes

Reaction equation

HRID 976332 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]2[O:18][C:17](=[O:19])[CH2:16][C@@H:15]([CH:20]=[CH2:21])[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O.C(#[N:31])C>>[NH2:31][N:2]=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]2[O:18][C:17](=[O:19])[CH2:16][C@@H:15]([CH:20]=[CH2:21])[CH2:14]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 70079702HCID 70079702, compound

Product 1

HCID 86750580HCID 86750580, compound

Procedure

The title compound was prepared from the product of step C (1.00g, 3.53 mmol) in a manner similar to example 1 step G with a modification in the purification. The residue was dissolved in acetonitrile and TFA (402 mg, 3.53 mmol) was added. The solvent was evaporated under reduced pressure and the residue redissolved in a minimal amount of acetonitrile. Addition of Et2O caused the precipitation of the crude product which was filtered and washed with Et2O. The material was briefly suspended in ice water, filtered, washed with ice water and dried. Recrystallization from acetonitrile afforded 720 mg (50%) of product as the TFA salt (m.p. 186°-187° C. dec.). Anal. calc'd. for C20N25O4F3 0.3H2O: C, 57.14; H, 6.15; N, 6.66.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue redissolved in a minimal amount of acetonitrile
  3. additionAddition of Et2O
  4. customthe precipitation of the crude product which
  5. filtrationwas filtered
  6. washwashed with Et2O
  7. filtrationfiltered
  8. washwashed with ice water
  9. customdried
  10. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-a741e89d44304ce6b4a8f646c7205167
Source dataset
uspto-grants-1997_03
Patent number
US05612355

Reaction notes

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