Ammonia → HCID 86608924, compound

HRID 2112406Notes

Reaction equation

HRID 2112406 reaction equation
CO[C:3]1[C:12]2=[CH:13][N:14]([C@@H:16]3[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@@:17]3([CH3:25])[OH:18])[N:15]=[C:10]3[C:11]2=[C:5]([C:6](=[O:26])[NH:7][N:8]=[CH:9]3)[N:4]=1.[NH3:27]>>[NH2:27][C:3]1[C:12]2=[CH:13][N:14]([C@@H:16]3[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@@:17]3([CH3:25])[OH:18])[N:15]=[C:10]3[C:11]2=[C:5]([C:6](=[O:26])[NH:7][N:8]=[CH:9]3)[N:4]=1

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 86608925HCID 86608925, compound

Product 1

HCID 86608924HCID 86608924, compoundYield 57%

Procedure

The product from Step 6 (20 mg, 0.0551 mmol) was dissolved in liquid ammonia (3 mL) at −78° C. then warmed to ambient temperature in a pressure vessel and stirred for 30 minutes. The reaction was then cooled to −78° C. and opened to allow the ammonia to evaporate. The residue was purified on Phenomenex-C18 reverse phase HPLC with a 0-50% B gradient over 30 min at 10 mL/min (Buffer A=H2O, Buffer B=acetonitrile) to afford 11 mg (57%) of the title compound.

Workup

  1. temperatureThe reaction was then cooled to −78° C.
  2. customto evaporate
  3. customThe residue was purified on Phenomenex-C18 reverse phase HPLC with a 0-50% B gradient over 30 min at 10 mL/min (Buffer A=H2O, Buffer B=acetonitrile)

Sources & evidence

ORD record
ord-86136fa0e51e44cc992b377cae717a60
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

Loading…